Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones

ABSTRACT

7Herbicidal 5-alkoxy-1,2,4-triazol-3-(thi)ones of the gerneral formula   &lt;IMAGE&gt; (I)  (in which the radicals R1, R2, R3, X and Y have the meanings given in the description), processes for their preparation, and their use as herbicides, and also new intermediates of the formula (II)   &lt;IMAGE&gt; (II)

This application is a continuation-in-part of application Ser. No.07/976,185, filed Nov. 6, 1992, now U.S. Pat. No. 5,356,865, which inturn is a continuation-in-part of application Ser. No. 07/757,785, filedNov. 11, 1991, now abandoned and is a continuation-in-part ofapplication Ser. No. 08/048,026, filed Apr. 15, 1993, now abandoned,which in turn is a continuation-in-part of application Ser. No.07/857,025, filed on Mar. 24, 1992, now abandoned, and this applicationfurther is a continuation-in-part of application Ser. No. 08/031,426,filed Mar. 15, 1993, now U.S. Pat. No. 5,405,970, which is a division ofapplication Ser. No. 07/816,365, filed Dec. 30, 1991, now U.S. Pat. No.5,241,074, which is a division of application Ser. No. 07/692,439, filedApr. 29, 1991, now U.S. Pat. No. 5,094,683, which is a division ofapplication Ser. No. 07/556,052, filed on Jul. 20, 1990 now U.S. Pat.No. 5,057,144, which is a continuation-in-part of Application Ser. No.07/337,775, filed on Apr. 13, 1989, now abandoned.

The invention relates to new substituted5-alkoxy-1,2,4-triazol-3-(thi)ones, a plurality of several processes,and also new intermediates for their preparation, and their use asherbicides.

This invention also relates to intermediates used to prepare newsulphonylaminocarbonyltriazolinones having substituents bonded viaoxygen which possess herbicidal activity. The final products aredisclosed in application Ser. No. 08/048,026, filed Apr. 15, 1993incorporated herein by reference.

It has been disclosed that certain substituted triazolones such as, forexample,4-amino-5-methyl-2-phenylaminocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one,have herbicidal properties (cf. EP-A 283,876, EP-A 294,666, EP-A298,371). However, the herbicidal activity of these compounds is notentirely satisfactory in all fields of application.

Further sulphonylaminocarbonyltriazolinones such as, for example,2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneare the subject of an earlier, but non-prior-published PatentApplication (cf. German Patent 3,934,081 dated Dec. 10, 1989).

New substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones of the generalformula (I) ##STR3## in which R¹ represents alkyl, alkenyl, alkinyl,halogenoalkyl, halogenoalkenyl, halogenoalkinyl, cyanoalkyl,hydroxyalkyl, alkoxyalkyl, alkoximinoalkyl, alkoxycarbonylalkyl,alkoxycarbonylalkenyl, alkylaminoalkyl or dialkylaminoalkyl, orrepresents in each case optionally substituted cycloalkyl,cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, or representsoptionally substituted heterocyclylalkyl, or represents alkoxy,alkenyloxy or alkinyloxy, or represents in each case optionallysubstituted aralkyl, aryloxyalkyl, aralalkenyl, arylalkinyl, aroyl,aryl, aralkyloxy or aryloxy.

R² represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl,halogenoalkinyl, alkoxyalkyl, cyanoalkyl, alkoxy, cycloalkyl orcycloalkylalkyl,

R³ represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl,halogenoalkinyl, alkoxyalkyl or cyanoalkyl,

X represents oxygen or sulphur and

Y represents oxygen or sulphur, have now been found.

Furthermore, it has been found that the new substituted5-alkoxy-1,2,4-triazol-3-(thi)ones of the general formula (I) areobtained when

(a) 5-alkoxy-1,2,4-triazol-3-(thi)ones of the general formula (II)##STR4## in which R², R³ and Y have the abovementioned meaning, arereacted with iso(thio)cyanates of the general formula (III)

    R.sup.1 --N═C═X                                    (III)

in which

R¹ and X have the abovementioned meanings, if appropriate in thepresence of a diluent and if appropriate in the presence of a basicreaction auxiliary, or when

(b) 5-alkoxy-1,2,4-triazol-3-(thi)ones of the general formula (II)##STR5## in which R², R³ and Y have the abovementioned meaning arereacted with reactive (thio-)carbamates of the general formula (IV)##STR6## in which R¹ and X have the abovementioned meanings and

R⁴ represents alkyl, aralkyl or aryl, if appropriate in the presence ofa diluent and if appropriate in the presence of a basic reactionauxiliary, or when

(c) 5-alkoxy-1,2,4-triazol-3-(thi)one derivatives of the general formula(V) ##STR7## in which R², R³, X and Y have the abovementioned meaningsand

R⁴ represents alkyl, aralkyl or aryl, are reacted with amino compoundsof the general formula (VI)

    R.sup.1 --NH.sub.2                                         (VI)

in which

R¹ has the abovementioned meaning, if appropriate in the presence of adiluent and if appropriate in the presence of a basic reactionauxiliary.

Finally, it has been found that the new substituted5-alkoxy-1,2,4-triazol-3-(thi)ones of the general formula (I) aredistinguished by powerful herbicidal activity.

Surprisingly, the new compounds of the formula (I) show a considerablybetter herbicidal activity than the compound4-amino-5-methyl-2-phenylaminocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one,which is known.

Additionally, there have been found novelsulphonylaminocarbonyltriazolinones having substitutuents bonded viaoxygen, of the general formula (X) ##STR8## in which R² representshydrogen, amino, or an optionally substituted radical from the seriescomprising alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl,alkylamino, cycloalkylamino, dialkylamino,

R³ represents an optionally substituted radical from the seriescomprising alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl,aryl, and

R^(a) represents an optionally substituted radical from the seriescomprising alkyl, aralkyl, aryl, heteroaryl,

and salts of compounds of the formula (X), with the exception of2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one(cf. German Patent 3,934,081).

Formula (I) provides a general definition of the substituted5-alkoxy-1,2,4-triazol-3-(thi)ones according to the invention. Preferredcompounds of the formula (I) are those in which

R¹ represents in each case straight-chain or branched alkyl having 1 to18 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17identical or different halogen atoms, halogenoalkenyl orhalogenoalkinyl, each of which has 2 to 8 carbon atoms and 1 to 15 or 13identical or different halogen atoms, cyanoalkyl having 1 to 8 carbonatoms, hydroxyalkyl having 1 to 8 carbon atoms and 1 to 6 hydroxylgroups, alkoxyalkyl, alkoximinoalkyl, alkoxycarbonylalkyl oralkoxycarbonylalkenyl, each of which has up to 6 carbon atoms in theindividual alkyl or alkenyl moieties, alkylaminoalkyl ordialkylaminoalkyl, each of which has 1 to 6 carbon atoms in theindividual alkyl moieties, or represents cycloalkyl, cycloalkylalkyl,cycloalkenyl or cycloalkenylalkyl, each of which has 3 to 8 carbon atomsin the cycloalkyl or cycloalkenyl moiety and if appropriate 1 to 6carbon atoms in the alkyl moiety and each of which is optionallymonosubstituted or polysubstituted by identical or differentsubstituents, the following being selected as preferred substituents inthe cyclic and optionally in the aliphatic moiety: halogen, cyano, andin each case straight-chain or branched alkyl or halogenoalkyl, each ofwhich has 1 to 4 carbon atoms and if appropriate 1 to 9 identical ordifferent halogen atoms, or in each case divalent alkanediyl oralkenediyl, each of which has up to 4 carbon atoms; R¹ furthermorerepresents heterocyclylalkyl which has 1 to 6 carbon atoms in thestraight-chain or branched alkyl moiety and 1 to 9 carbon atoms as wellas 1 to 3 hetero atoms--in particular nitrogen, oxygen and/orsulphur--in the heterocyclyl moiety and each of which is optionallymonosubstituted or polysubstituted by identical or differentsubstituents, the following being selected as preferred substituents:halogen, cyano, nitro, and in each case straight-chain or branchedalkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy,halogenoalkylthio or alkoxycarbonyl, each of which has 1 to 5 carbonatoms and if appropriate 1 to 9 identical or different halogen atoms; R¹furthermore represents in each case straight-chain or branched alkoxyhaving 1 to 8 carbon atoms, alkenyloxy having 2 to 8 carbon atoms oralkinyloxy having 2 to 8 carbon atoms, and finally represents aralkyl,aryloxyalkyl, arylalkenyl, arylakinyl, aralkyloxy, aryloxy, aroyl oraryl, each of which has 6 or 10 carbon atoms in the aryl moiety and ifappropriate up to 8 carbon atoms in the alkyl, alkenyl or alkinylmoiety, and each of which is optionally monosubstituted orpolysubstituted by identical or different substituents, suitable arylsubstituents in each case being: halogen, cyano, nitro, hydroxyl, ineach case straight-chain or branched alkyl, alkoxy, alkylthio,halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylsulphinyl,alkylsulphonyl, halogenoalkylsulphinyl, halogenoalkylsulphonyl, alkanoylor alkoxycarbonyl, each of which has 1 to 6 carbon atoms and ifappropriate 1 to 9 identical or different halogen atoms, cycloalkylhaving 3 to 6 carbon atoms and phenoxy, and suitable optional alkylsubstituents being: halogen or cyano,

R² represents in each case straight-chain or branched alkyl having 1 to8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17identical or different halogen atoms, halogenoalkenyl having 2 to 8carbon atoms and 1 to 15 identical or different halogen atoms,halogenoalkinyl having 2 to 8 carbon atoms and 1 to 13 identical ordifferent halogen atoms, alkoxyalkyl or alkoxy, each of which has 1 to 6carbon atoms in the individual alkyl moieties, cyanoalkyl having 1 to 8carbon atoms, or represents cycloalkylalkyl or cycloalkyl, each of whichhas 3 to 7 carbon atoms in the cycloalkyl moiety and if appropriate 1 to6 carbon atoms in the straight-chain or branched alkyl moiety,

R³ represents in each case straight-chain or branched alkyl having 1 to8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17identical or different halogen atoms, halogenoalkenyl having 2 to 8carbon atoms and 1 to 15 identical or different halogen atoms,halogenoalkinyl having 2 to 8 carbon atoms and 1 to 13 identical ordifferent halogen atoms, alkoxyalkyl having 1 to 6 carbon atoms in eachof the individual alkyl moieties, or represents cyanoalkyl having 1 to 8carbon atoms,

X represents oxygen or sulphur and

Y represents oxygen or sulphur and halogen in the substitution patternsmentioned in the case of R¹, R² and R³ represents fluorine, chlorine,bromine and iodine.

Particularly preferred compounds of the formula (I) are those in which

R¹ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ineach case straight-chain or branched pentyl, hexyl, heptyl, octyl,nonyl, decyl or dodecyl, or represents allyl, propenyl, n- or i-butenyl,n- or i-pentenyl, n- or i-hexenyl, propargyl, n- or i-butinyl, n- ori-pentinyl, n- or i-hexinyl, or represents straight-chain or branchedhalogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical ordifferent halogen atoms, in particular fluorine, chlorine or bromine, orrepresents in each case straight-chain or branched halogenoalkenyl orhalogenoalkinyl, each of which has 3 to 5 carbon atoms and 1 to 3halogen atoms, in particular fluorine or chlorine, or represents in eachcase straight-chain or branched cyanoalkyl having 1 to 4 carbon atoms inthe alkyl moiety, hydroxyalkyl having 1 to 6 carbon atoms and 1 to 3hydroxyl groups, alkoxyalkyl, alkoximinoalkyl, alkoxycarbonylalkyl oralkoxycarbonylalkenyl, alkylaminoalkyl or dialkylaminoalkyl, each ofwhich has up to 4 carbon atoms in the individual alkyl or alkenylmoieties, or represents cyclopropyl, cyclopropylmethyl,cyclopropylethyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl,cyclohexenyl or cyclohexenylmethyl, each of which is optionallymonosubstituted to trisubstituted by identical or differentsubstituents, the following being selected as particularly preferredsubstituents in the cyclic and if appropriate in the aliphatic moiety:fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, cyano, methanediyl, ethanediyl, butanediyl or butadienediyl;R¹ furthermore represents heterocyclylinethyl, heterocyclylethyl orheterocyclylpropyl, each of which is optionally monosubstituted totrisubstituted in the heterocyclyl moiety by identical or differentsubstituents, suitable heterocycles in each case being: ##STR9## where Zin each case represents oxygen or sulphur and where the following areselected as particularly preferred substituents:

fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio,trifluoromethyl, trifluoromethoxy or trifluoromethylthio; R¹ furthermorerepresents in each case straight-chain or branched alkoxy having 1 to 6carbon atoms, alkenyloxy having 3 to 6 carbon atoms or alkinyloxy having3 to 6 carbon atoms, or represents benzyl, phenylethyl, phenylpropyl,phenylbutyl, phenylpentyl, phenylhexyl, phenylheptyl, phenylcyanomethyl,phenylcyanoethyl, phenylcyanopropyl, phenoxymethyl, phenoxyethyl,phenoxypropyl, phenoxybutyl, phenylethinyl, benzyloxy, phenylethyloxy,phenoxy, benzoyl, phenyl or naphthyl, if appropriate straight-chain orbranched, each of which is optionally monosubstituted to trisubstitutedby identical or different substituents, suitable phenyl substituents ineach case being: fluorine, chlorine, bromine, hydroxyl, cyano, nitro,methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy,methylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy,trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl,methylsulphinyl, methylsulphonyl, acetyl, propionyl, methoxycarbonyl,ethoxycarbonyl, cyclohexyl and phenoxy,

R² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-or i-pentyl, n- or i-hexyl, or represents allyl, propargyl, methoxy,ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl or ethoxyethyl, orrepresents straight-chain or branched halogenoalkyl, halogenoalkenyl andhalogenoalkinyl having 1 to 4 carbon atoms and 1 to 9 identical ordifferent halogen atoms, in particular fluorine, chlorine or bromine, orrepresents cyclopentyl, cyclohexyl, cyclopropyl, cyclopropylmethyl,cyclopentylmethyl, cyclohexylmethyl or cyclohexylethyl,

R³ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-,i-, s- or t-pentyl, n- or i-hexyl, or represents allyl, propargyl,methoxyethyl, ethoxyethyl, fluoroethyl, chloroethyl, fluoropropyl,chloropropyl or cyanoethyl,

X represents oxygen or sulphur and

Y represents oxygen or sulphur.

Very particularly preferred compounds of the formula (I) are those inwhich

R¹ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-,i-, s- or t-pentyl, n-, i-, s- or t-hexyl, propargyl, n- or i-butinyl,n- or i-pentinyl, or represents straight-chain or branched halogenoalkylhaving 1 to 4 carbon atoms and 1 to 4 identical or different halogenatoms, in particular fluorine and chlorine, or represents cyanomethyl,cyanoethyl or n- or i-cyanopropyl, or represents cyclopropyl,cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl orcyclohexylmethyl, each of which is optionally monosubstituted totrisubstituted by identical or different substituents, or representsphenyl, benzyl or phenylethyl, each of which is optionallymonosubstituted to trisubstituted by identical or different substituentsfrom the series comprising fluorine, chlorine, bromine, methyl, ethyland/or trifluoromethyl, or represents in each case straight-chain orbranched phenylpropyl, phenylbutyl, phenylpentyl or phenylhexyl, orrepresents morpholinyl-C₁ -C₄ -alkyl,

R² represents methyl, ethyl, n-, i- or cyclopropyl, n-, i-, s- ort-butyl,

R³ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-or i-pentyl,

X represents oxygen and

Y represents oxygen.

The new sulphonylaminocarbonyltriazolinones having substituents bondedvia oxygen, of the general formula (X), are obtained when

(a) triazolinones of the general formula (II) ##STR10## in which R² andR³ have the abovementioned meanings are reacted with sulphonylisocyanates of the general formula (XI)

    R.sup.a --SO.sub.2 --N═C═O                         (XI)

in which

R^(a) has the abovementioned meaning, if appropriate in the presence ofa diluent, or when

(b) triazolinone derivatives of the general formula (XII) ##STR11## inwhich R² and R³ have the abovementioned meanings and

Z¹ represents halogen, alkoxy, aralkoxy or aryloxy, are reacted withsulphonamides of the general formula (XIII)

    R.sup.3 --SO.sub.2 --NH.sub.2                              (XIII)

in which

R^(a) has the abovementioned meaning, if appropriate in the presence ofan acid acceptor and if appropriate in the presence of a diluent, orwhen

(c) triazolinones of the general formula (II) ##STR12## in which R² andR³ have the abovementioned meanings are reacted with sulphonamidederivatives of the general formula (XIV)

    R.sup.a --SO.sub.2 --NH--CO--Z                             (XIV)

in which

R^(a) has the abovementioned meaning and

Z¹ represents halogen, alkoxy, aralkoxy or aryloxy, if appropriate inthe presence of an acid acceptor and if appropriate in the presence of adiluent and, if appropriate, salts are formed, by customary methods, ofthe compounds of the formula (I) which have been prepared by process(a), (b) or (c).

The new sulphonylaminocarbonyltriazolinones having substituents bondedvia oxygen, of the general formula (I), and their salts aredistinguished by a powerful herbicidal activity.

Surprisingly, the new compounds of the formula (X) show a considerablybetter herbicidal action than the known compound2-(2-chlorophenylsulphonylaminocarbonyl)-4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one,which has a similar structure.

The invention preferably relates to compounds of the formula (X) inwhich

R² represents hydrogen, amino, or represents C₁ -C₆ -alkyl which isoptionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄-alkoxy, C₁ -C₄ -alkylcarbonyl or C₁ -C₄ -alkoxy-carbonyl, or representsC₃ -C₆ -alkenyl or C₃ C₆ -alkinyl, each of which is optionallysubstituted by fluorine, chlorine and/or bromine, or represents C₃ -C₆-cycloalkyl which is optionally substituted by fluorine, chlorine,bromine and/or C₁ -C₄ -alkyl, or represents phenyl-C₁ -C₃ -alkyl whichis optionally substituted by fluorine, chlorine, bromine, cyano, nitro,C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy and/or C₁ -C₄-alkoxy-carbonyl, or represents phenyl which is optionally substitutedby fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl,trifluoromethyl, C₁ -C₄ -alkoxy, fluorine- and/or chlorine-substitutedC₁ -C₃ -alkoxy, C₁ -C₄ -alkylthio, fluorine- and/or chlorine-substitutedC₁ -C₃ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl and/orC₁ -C₄ -alkoxycarbonyl, or represents C₁ -C₄ -alkylamino which isoptionally substituted by fluorine, cyano, C₁ -C₄ -alkoxy or C₁ -C₄-alkoxy-carbonyl, or represents C₃ -C₆ -cycloalkylamino or di-(C₁ -C₄-alkyl)-amino,

R³ represents C₁ -C₆ -alkyl which is optionally substituted by fluorine,chlorine, bromine, cyano, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxy or C₁ -C₄-alkoxycarbonyl, or represents C₃ -C₆ -alkenyl or C₃ -C₆ -alkinyl, eachof which is optionally substituted by fluorine, chlorine and/or bromine,or represents C₃ -C₆ -cycloalkyl which is optionally substituted byfluorine, chlorine, bromine and/or C₁ -C₄ -alkyl, or representscyclohexenyl, or represents phenyl-C₁ -C₃ -alkyl which is optionallysubstituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl,trifluoromethyl, C₁ -C₄ -alkoxy and/or C₁ -C₄ -alkoxy-carbonyl, orrepresents phenyl which is optionally substituted by fluorine, chlorine,bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy,fluorine- and/or chlorine-substituted C₁ -C₃ -alkoxy, C₁ -C₄ -alkylthio,fluorine- and/or chlorine-substituted C₁ -C₃ -alkylthio, C₁ -C₄-alkyl-sulphinyl, C₁ -C₄ -alkylsulphonyl and/or C₁ -C₄ -alkoxy-carbonyl,and

R^(a) represents the group ##STR13## in which R⁴.spsp.1 and R⁵ areidentical or different and represent hydrogen, fluorine, chlorine,bromine, iodine, nitro, C₁ -C₆ -alkyl (which is optionally substitutedby fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxycarbonyl,C₁ -C₄ -alkylamino-carbonyl, di- (C₁ -C₄ -alkyl) amino-carbonyl,hydroxyl, C₁ -C₄ -alkoxy, formyloxy, C₁ -C₄ -alkyl-carbonyloxy, C₁ -C₄-alkoxy-carbonyloxy, C₁ -C₄ -alkylamino-carbonyloxy, C₁ -C₄ -alkylthio,C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, di- (C₁ -C₄-alkyl)-aminosulphonyl, C₃ -C₆ -cycloalkyl or phenyl), or represent C₂-C₆ -alkenyl (which is optionally substituted by fluorine, chlorine,bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), orrepresent C₂ -C₆ -alkinyl (which is optionally substituted by fluorine,chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl),or represent C₁ -C₄ -alkoxy (which is optionally substituted byfluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl,C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄-alkylsulphonyl), or represent C₁ -C₄ -alkylthio (which is optionallysubstituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄-alkoxy-carbonyl, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄-alkylsulphonyl), or represent C₃ -C₆ -alkenyloxy (which is optionallysubstituted by fluorine, chlorine, bromine, cyano or C₁ -C₄-alkoxy-carbonyl), or represent C₂ -C₆ -alkenylthio (which is optionallysubstituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₃-alkylthio or C₁ -C₄ -alkoxycarbonyl), C₃ -C₆ -alkinyloxy, C₃ -C₆-alkinylthio or the radical --S(O)_(p) --R⁶ where

p represents the numbers 1 or 2 and

R⁶ represents C₁ -C₄ -alkyl (which is optionally substituted byfluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxy-carbonyl), C₃ -C₆-alkenyl, C₃ -C₆ -alkinyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄-alkylamino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino, phenyl or theradical --NHOR⁷ where

R⁷ represents C₁ -C₁₂ -alkyl (which is optionally substituted byfluorine, chlorine, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkyl-carbonyl, C₁ -C₄-alkoxy-carbonyl, C₁ -C₄ -alkylamino-carbonyl or di-(C₁ -C₄-alkyl)-amino-carbonyl), or represents C₃ -C₆ -alkenyl (which isoptionally substituted by fluorine, chlorine or bromine),C₃ -C₆-alkinyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₂ -alkyl,phenyl-C₁ -C₂ -alkyl (which is optionally substituted by fluorine,chlorine, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄-alkoxy-carbonyl), or represents benzhydryl, or represents phenyl (whichis optionally substituted by fluorine, chlorine, nitro, cyano, C₁ -C₄-alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, C₁ -C₂ -fluoroalkoxy, C₁ -C₄-alkylthio, trifluoromethylthio or C₁ -C₄ -alkoxy-carbonyl),

R⁴.spsp.1 and/or R⁵ furthermore represent phenyl or phenoxy, orrepresent C₁ -C₄ -alkylcarbonylamino, C₁ -C₄ -alkoxy-carbonylamino, C₁-C₄ -alkylamino-carbonyl-amino, di-(C₁ -C₄ -alkyl)-amino-carbonylamino,or the radical --CO--R⁸ where

R⁸ represents C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -cycloalkoxy, C₃ -C₆-alkenyloxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylamino, C₁ -C₄ -alkoxyamino,C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl-amino or di-(C₁ -C₄ -alkyl)-amino (whichare optionally substituted by fluorine and/or chlorine),

R⁴.spsp.1 and/or R⁵ furthermore represent trimethylsilyl, thiazolinyl,C₁ -C₄ -alkylsulphonyloxy, di-(C₁ -C₄ -alkyl)aminosulphonylamino or theradical --CH═N--R⁹ where

R⁹ represents C₁ -C₆ -alkyl which is optionally substituted by fluorine,chlorine, cyano, carboxyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl or C₁ -C₄ -alkylsulphonyl, or represents benzyl which isoptionally substituted by fluorine or chlorine, or represents C₃ -C₆-alkenyl or C₃ -C₆ -alkinyl, each of which is optionally substituted byfluorine or chlorine, or represents phenyl which is optionallysubstituted by fluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄-alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, orrepresents optionally fluorine- and/or chlorine-substituted C₁ -C₆-alkoxy, C₃ -C₆ -alkenoxy, C₃ -C₆ -alkinoxy or benzyloxy, or representsamino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino, phenylamino, C₁ -C₄-alkyl-carbonyl-amino, C₁ -C₄ -alkoxycarbonylamino or C₁ -C₄-alkyl-sulphonylamino, or represents phenylsulphonylamino which isoptionally substituted by fluorine, chlorine, bromine or methyl,

furthermore

R^(a) represents the radical ##STR14## where R¹⁰ represents hydrogen orC₁ -C₄ -alkyl,

R¹¹ and R¹² are identical or different and represent hydrogen, fluorine,chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionallysubstituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which isoptionally substituted by fluorine and/or chlorine), carboxyl, C₁ -C₄-alkoxy-carbonyl, dimethylaminocarbonyl, C₁ -C₄ -alkylsulphonyl ordi-(C₁ -C₄ -alkyl) -aminosulphonyl;

furthermore

R^(a) represents the radical ##STR15## where R¹³ and R¹⁴ are identicalor different and represent hydrogen, fluorine, chlorine, bromine, nitro,cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/orchlorine) or C₁ -C₄ -alkoxy (which is optionally substituted by fluorineand/or chlorine);

furthermore

R^(a) represents the radical ##STR16## where R¹⁵ and R¹⁶ are identicalor different and represent hydrogen, fluorine, chlorine, bromine, nitro,cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/orchlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorineand/or chlorine), or represent C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinylor C₁ -C₄ -alkylsulphonyl (which are optionally substituted by fluorineand/or chlorine), or represent aminosulphonyl, mono-(C₁ -C₄-alkyl)-aminosulphonyl, di-(C₁ -C₄ -alkyl)-aminosulphonyl or C₁ -C₄-alkoxycarbonyl or dimethylaminocarbonyl;

furthermore

R^(a) represents the radical ##STR17## where R¹⁷ and R¹⁸ are identicalor different and represent hydrogen, fluorine, chlorine, bromine, C₁ -C₄-alkyl (which is optionally substituted by fluorine and/or bromine), C₁-C₄ -alkoxy (which is optionally substituted by fluorine and/orchlorine), C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄-alkylsulphonyl (which are optionally substituted by fluorine and/orchlorine), or represent di-(C₁ -C₄ -alkyl)-aminosulphonyl;

furthermore

R^(a) represents the radical ##STR18## where R¹⁹ and R²⁰ are identicalor different and represent hydrogen, fluorine, chlorine, bromine, cyano,nitro, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/orchlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorineand/or chlorine), C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄-alkylsulphonyl (which is optionally substituted by fluorine and/orchlorine), di-(C₁ -C₄ -alkyl)-amino-sulphonyl, C₁ -C₄ -alkoxy-carbonylor dimethylaminocarbonyl, and

A represents oxygen, sulphur or the group N--Z¹, where

Z¹ represents hydrogen, C₁ -C₄ -alkyl (which is optionally substitutedby fluorine, chlorine, bromine or cyano), C₃ -C₆ -cycloalkyl, benzyl,phenyl (which is optionally substituted by fluorine, chlorine, bromineor nitro), C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-carbonyl or di-(C₁ -C₄-alkyl) -aminocarbonyl;

furthermore

R^(a) represents the radical ##STR19## where R²¹ and R²² are identicalor different and represent hydrogen, C₁ -C₄ -alkyl, halogen, C₁ -C₄-alkoxycarbonyl, C₁ -C₄ -alkoxy or C₁ -C₄ -halogenoalkoxy,

Y¹ represents sulphur or the group N--R²³, where

R²³ represents hydrogen or C₁ -C₄ -alkyl;

furthermore

R^(a) represents the radical ##STR20## where R²⁴ represents hydrogen, C₁-C₄ -alkyl, benzyl, pyridyl, quinolinyl or phenyl,

R²⁵ represents hydrogen, halogen, cyano, nitro, C₁ -C₄ -alkyl (which isoptionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy(which is optionally substituted by fluorine and/or chlorine),dioxolanyl or C₁ -C₄ -alkoxy-carbonyl and

R²⁶ represents hydrogen, halogen or C₁ -C₄ -alkyl;

furthermore

R^(a) represents one of the groups listed below ##STR21##

The invention furthermore preferably relates to the sodium, potassium,magnesium, calcium, ammonium, C₁ -C₄ -alkyl-ammonium, di-(C₁ -C₄-alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-ammonium, C₅ - or C₆-cycloalkyl-ammonium and di-(C₁ -C₂ -alkyl) -benzyl-ammonium salts ofcompounds of the formula (I) in which R¹, R² and R³ have the meaningsmentioned above as being preferred.

In particular, the invention relates to compounds of the formula (X) inwhich

R² represents hydrogen, amino, C₁ -C₄ -alkyl which is optionallysubstituted by fluorine, cyano, methoxy or ethoxy, or represents allyl,C₃ -C₆ -cycloalkyl, benzyl, phenyl, C₁ -C₃ -alkylamino, C₃ -C₆-cycloalkylamino or di-(C₁ -C₃ -alkyl) -amino,

R³ represents C₁ -C₄ -alkyl which is optionally substituted by fluorineand/or chlorine, methoxy or ethoxy, or represents C₃ -C₄ -alkenyl whichis optionally substituted by fluorine and/or chlorine, or represents C₃-C₆ -cycloalkyl, or represents benzyl which is optionally substituted byfluorine, chlorine and/or methyl, and

R^(a) represents the group ##STR22## where R⁴.spsp.1 representsfluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy,difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxyethoxy, C₁-C₃ -alkylthio, C₁ -C₃ -alkylsulphinyl, C₁ -C₃ -alkylsulphonyl,dimethylaminosulphonyl, diethylaminosulphonyl,N-methoxy-N-methylaminosulphonyl, methoxyaminosulphonyl, phenyl, phenoxyor C₁ -C₃ -alkoxy-carbonyl and

R⁵ represents hydrogen, fluorine, chlorine or bromine;

furthermore

R^(a) represents the radical ##STR23## where R¹⁰ represents hydrogen,

R¹¹ represents fluorine, chlorine, bromine, methyl, methoxy,difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl,ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl and

R¹² represents hydrogen;

furthermore

R^(a) represents the radical ##STR24## where R represents C₁ -C₄ -alkyl,or represents the radical ##STR25## where R represents C₁ -C₄ -alkyl.

The abovementioned definitions of radicals, in general or mentioned inpreferred ranges, can be combined with each other in any desired way,that is to say also between the particular preferred ranges.

Examples of the compounds of the formula (I) according to the inventionare listed in Table 1 below. ##STR26##

                  TABLE 1                                                         ______________________________________                                        Examples of the compounds of the formula (I)                                  R.sup.1                R.sup.2                                                                              R.sup.3                                                                              X   Y                                    ______________________________________                                        i-C.sub.3 H.sub.7      CH.sub.3                                                                             CH.sub.3                                                                             O   O                                    CF.sub.3C(CH.sub.3).sub.2                                                                            CH.sub.3                                                                             C.sub.2 H.sub.5                                                                      O   O                                    FCH.sub.2C(CH.sub.3).sub.2                                                                           CH.sub.3                                                                             C.sub.2 H.sub.5                                                                      O   O                                    C.sub.2 H.sub.5 C(CH.sub.3).sub.2                                                                    CH.sub.3                                                                             CH.sub.3                                                                             O   O                                    C.sub.3 H.sub.7C(CH.sub.3).sub.2                                                                     CH.sub.3                                                                             CH.sub.3                                                                             O   O                                    i-C.sub.3 H.sub.7C(CH.sub.3).sub.2                                                                   CH.sub.3                                                                             CH.sub.3                                                                             O   O                                                           CH.sub.3                                                                             CH.sub.3                                                                             O   O                                     ##STR27##             CH.sub.3                                                                             CH.sub.3                                                                             O   O                                     ##STR28##             CH.sub.3                                                                             CH.sub.3                                                                             O   O                                     ##STR29##             CH.sub.3                                                                             CH.sub.3                                                                             O   O                                     ##STR30##             CH.sub.3                                                                             CH.sub.3                                                                             O   O                                     ##STR31##             CH.sub.3                                                                             CH.sub.3                                                                             O   O                                     ##STR32##             CH.sub.3                                                                             C.sub.2 H.sub.5                                                                      O   O                                     ##STR33##             CH.sub.3                                                                             CH.sub.3                                                                             O   O                                    ______________________________________                                    

If, for example, 5-ethoxy-4-ethyl-2,4-dihydro-3H-1,2,4-triazole-3-thioneand isopropyl-isocyanate are used as starting substances, the course ofthe reaction of process (a) according to the invention can beillustrated by the following equation: ##STR34##

If, for example,5-isopropoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one andO-Methyl-N-tert.-butylthiocarbamate are used as starting substances, thecourse of the reaction of process (b) according to the invention can beillustrated by the following equation: ##STR35##

If, for example,4-isopropyl-5-methoxy-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-oneand cyclohexylamine are used as starting substances, the course of thereaction of process (c) according to the invention can be illustrated bythe following equation: ##STR36##

Formula (II) provides a general definition of the5-alkoxy-1,2,4-triazol-3-(thi)ones to be used as starting substances inprocesses (a) and (b) according to the invention for the preparation ofcompounds of the formula (I).

In formula (II), R², R³ and Y preferably, or in particular, have thosemeanings which have already been mentioned above in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, or as particularly preferred, for R², R³and Y.

Examples of the compounds of formula X are listed in Table 2 below--cf.also the Preparation Examples ##STR37##

                                      TABLE 2                                     __________________________________________________________________________    Examples of the compounds of the formula (X)                                  R.sup.2   R.sup.3    R.sup.a                                                  __________________________________________________________________________              CH.sub.3                                                                                  ##STR38##                                                ##STR39##                                                                              CH.sub.3                                                                                  ##STR40##                                               CH.sub.3  C.sub.2 H.sub.5                                                                           ##STR41##                                               CH.sub.3  CH.sub.2CHCH.sub.2                                                                        ##STR42##                                               CH.sub.3  CH.sub.3                                                                                  ##STR43##                                               CH.sub.3  CH.sub.3                                                                                  ##STR44##                                               CH.sub.3  C.sub.2 H.sub.5                                                                           ##STR45##                                               CH.sub.3  C.sub.2 H.sub.5                                                                           ##STR46##                                               CH.sub.3  C.sub.2 H.sub.5                                                                           ##STR47##                                               C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           ##STR48##                                               C.sub.2 H.sub.5                                                                         C.sub.3 H.sub.7                                                                           ##STR49##                                                ##STR50##                                                                              CH.sub.3                                                                                  ##STR51##                                                ##STR52##                                                                              C.sub.2 H.sub.5                                                                           ##STR53##                                                ##STR54##                                                                              CH(CH.sub.3).sub.2                                                                        ##STR55##                                               CH.sub.3  CH(CH.sub.3).sub.2                                                                        ##STR56##                                               CH.sub.3  CH.sub.2CHCH.sub.2                                                                        ##STR57##                                               C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                  ##STR58##                                               C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           ##STR59##                                               CH.sub.3  C.sub.2 H.sub.5                                                                           ##STR60##                                               C.sub.2 H.sub.5                                                                         C.sub.3 H.sub.7                                                                           ##STR61##                                               CH.sub.2  C.sub.2 H.sub.5                                                                           ##STR62##                                                ##STR63##                                                                              CH.sub.3                                                                                  ##STR64##                                                ##STR65##                                                                              C.sub.2 H.sub.5                                                                           ##STR66##                                                ##STR67##                                                                              CH.sub.3                                                                                  ##STR68##                                                ##STR69##                                                                              C.sub.2 H.sub.5                                                                           ##STR70##                                                ##STR71##                                                                              C.sub.3 H.sub.7 -n                                                                        ##STR72##                                               CH.sub.3  C.sub.2 H.sub.5                                                                           ##STR73##                                               CH.sub.3  CH.sub.3                                                                                  ##STR74##                                               CH.sub.3  C.sub.2 H.sub.5                                                                           ##STR75##                                               CH.sub.3                                                                                 ##STR76##                                                                                ##STR77##                                               CH.sub.3  C.sub.2 H.sub.5                                                                           ##STR78##                                                ##STR79##                                                                              C.sub.2 H.sub.5                                                                           ##STR80##                                                ##STR81##                                                                              CH.sub.3                                                                                  ##STR82##                                               CH.sub.3  CH.sub.3                                                                                  ##STR83##                                               CH.sub.3  C.sub.3 H.sub.7                                                                           ##STR84##                                               C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           ##STR85##                                               CH.sub.2CHCH.sub.2                                                                      C.sub.2 H.sub.5                                                                           ##STR86##                                               CH.sub.2CHCH.sub.2                                                                      CH.sub.3                                                                                  ##STR87##                                               C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                  ##STR88##                                               C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           ##STR89##                                               C.sub.3 H.sub.7                                                                         CH.sub.2CHCH.sub.2                                                                        ##STR90##                                               CH.sub.3  CH.sub.3                                                                                  ##STR91##                                                ##STR92##                                                                              C.sub.2 H.sub.5                                                                           ##STR93##                                                ##STR94##                                                                              C.sub.2 H.sub.5                                                                           ##STR95##                                               C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           ##STR96##                                               CH.sub.3  C.sub.2 H.sub.5                                                                           ##STR97##                                               CH.sub.3  C.sub.3 H.sub.7                                                                           ##STR98##                                               C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                  ##STR99##                                               C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                  ##STR100##                                              C.sub.3 H.sub.7                                                                         C.sub.2 H.sub.5                                                                           ##STR101##                                              C.sub.3 H.sub.7                                                                         C.sub.2 H.sub.5                                                                           ##STR102##                                              CH.sub.3  C.sub.2 H.sub.5                                                                           ##STR103##                                              CH.sub.3  CH.sub.3                                                                                  ##STR104##                                              N(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                  ##STR105##                                              CH.sub.3  C.sub.2 H.sub.5                                                                           ##STR106##                                              C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           ##STR107##                                               ##STR108##                                                                             CH.sub.3                                                                                  ##STR109##                                              CH.sub.3  C.sub.2 H.sub.5                                                                           ##STR110##                                              N(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                  ##STR111##                                              __________________________________________________________________________

If, for example, 2,6-difluoro-phenylsulphonyl isocyanate and5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are used asstarting substances, the course of the reaction in process (a) accordingto the invention can be outlined by the following equation: ##STR112##

If, for example, 2-methylthio-benzenesulphonamide and2-chlorocarbonyl-4-dimethylamino-5-propyloxy-2,4-dihydro-3H-1,2,4-triazol-3-oneare used as starting substances, the course of the reaction in process(b) according to the invention can be outlined by the followingequation: ##STR113##

If, for example, N-methoxycarbonyl-2-methoxy-benzenesulphonamide and5-methoxy-4-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one are usedas starting substances, the course of the reaction in process (c)according to the invention can be outlined by the following equation:##STR114##

Formula (II) provides a general definition of the triazolinones to beused as starting substances in processes (a) and (c) according to theinvention for the preparation of compounds of the formula (X).

In formula (II), R² and R³ preferably, or in particular, have thosemeanings which have already been mentioned above in connection with thedescription of the compounds of the formula (X) according to theinvention as being preferred, or particularly preferred, for R² and R³.

Examples of the starting substances of the formula (II) are listed inTable 3 below. ##STR115##

                  TABLE 2                                                         ______________________________________                                        Examples of the starting substances of the                                    formula (II)                                                                  R.sup.2    R.sup.3       γ                                              ______________________________________                                        CH.sub.3   CH.sub.3      O                                                    CH.sub.3   CH.sub.3      S                                                    CH.sub.3   C.sub.2 H.sub.5                                                                             O                                                    CH.sub.3   C.sub.2 H.sub.5                                                                             S                                                    CH.sub.3   C.sub.3 H.sub.7                                                                             O                                                    CH.sub.3   C.sub.3 H.sub.7                                                                             S                                                    CH.sub.3   CH(CH.sub.3).sub.2                                                                          O                                                    CH.sub.3   CH(CH.sub.3).sub.2                                                                          S                                                    CH.sub.3   --CH.sub.2 --CH═CH.sub.2                                                                S                                                    CH.sub.3   --CH.sub.2 --CH═CH.sub.2                                                                S                                                    C.sub.2 H.sub.5                                                                          CH.sub.3      O                                                    C.sub.2 H.sub.5                                                                          CH.sub.3      S                                                    C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                             O                                                    C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                             S                                                    C.sub.2 H.sub.5                                                                          CH(CH.sub.3).sub.2                                                                          O                                                    C.sub.2 H.sub.5                                                                          --CH.sub.2 --CH═CH.sub.2                                                                O                                                    C.sub.2 H.sub.5                                                                          CH(CH.sub.3).sub.2                                                                          S                                                    C.sub.2 H.sub.5                                                                          --CH.sub.2 --CH═CH.sub.2                                                                S                                                    ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                        Examples of the starting substances of the                                    formula (II)                                                                  R.sup.2           R.sup.3      Y                                              ______________________________________                                        H                 CH.sub.3     O                                              CH.sub.3          CH.sub.3     O                                              C.sub.2 H.sub.5   CH.sub.3     O                                              C.sub.3 H.sub.7   CH.sub.3     O                                              CH(CH.sub.3).sub.2                                                                              CH.sub.3     O                                              C.sub.4 H.sub.9   CH.sub.3     O                                               ##STR116##       CH.sub.3     O                                              CH.sub.3                                                                                         ##STR117##  O                                              CH.sub.3                                                                                         ##STR118##  O                                              C.sub.3 H.sub.7   C.sub.2 H.sub.5                                                                            O                                               ##STR119##       C.sub.2 H.sub.5                                                                            O                                              CH.sub.2CHCH.sub.2                                                                              C.sub.2 H.sub.5                                                                            O                                              CH.sub.2CHBrCH.sub.2 Br                                                                         C.sub.2 H.sub.5                                                                            O                                               ##STR120##       C.sub.3 H.sub.7                                                                            O                                               ##STR121##       CH.sub.2CHCH.sub.2                                                                         O                                               ##STR122##       CH(CH.sub.3).sub.2                                                                         O                                              C.sub.3 H.sub.7   CH(CH.sub.3).sub.2                                                                         O                                              CH.sub.2CHCH.sub.2                                                                              C.sub.3 H.sub.7                                                                            O                                              C.sub.2 H.sub.5   C.sub.3 H.sub.7                                                                            O                                              C.sub.2 H.sub.5                                                                                  ##STR123##  O                                              C.sub.3 H.sub.7   C.sub.3 H.sub.7                                                                            O                                              ______________________________________                                    

The starting substances of the formula (II) are known in some cases (cf.J. Chem. Soc C 1967, 2700-2704; J. Heterocycl. Chem. 15 (1978), 377-384)subject of an earlier, but non-prior-published, Patent Application (cf.German Patent 4,030,063, dated

Those compounds of the general formula (II) in which Y represents oxygenand R² and R³ have the abovementioned meanings are new and are a subjectof the present patent application.

The new 5-alkoxy-1,2,4-triazol-3-ones (II, Y=O) are obtained whenhydrazinoformic esters of the general formula (VII)

    H.sub.2 N--NH--CO--O--R.sup.4                              (VII)

in which

R⁴ has the abovementioned meaning are reacted with alkyliminocarboxylicdiesters of the general formula (VIII) ##STR124## in which R² and R³have the abovementioned meaning, if appropriate in the presence of adiluent such as, for example, o-dichlorobenzene, at temperatures between0° C. and 200° C., preferably between 50° C. and 150° C. (cf. thePreparation Examples).

The starting substances of the formulae (VII) and (VIII) are knownchemicals.

Formula (III) provides the general definition of the iso(thio)cyanatesto be used as starting substances in process (a) according to theinvention for the preparation of compounds of the formula (I).

In formula (III), R¹ and X preferably, or in particular, have thosemeanings which have already been mentioned above in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, or as particularly preferred, for R¹ andX.

The starting substances of the formula (III) are known chemicals fororganic synthesis.

Formula (IV) provides a general definition of the reactive(thio)carbamates to be used as starting substances in process (b)according to the invention for the preparation of compounds of theformula (I).

In formula (IV), R¹ and X preferably, or in particular, have thosemeanings which have already been mentioned above in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, or as particularly preferred, for R¹ andX;

R⁴ preferably represents methyl, ethyl, phenyl or benzyl.

The starting substances of the formula (IV) are known chemicals fororganic synthesis.

Formula (V) provides a general definition of the5-alkoxy-1,2,4-triazol-3-(thi)one derivatives to be used as startingsubstances in process (c) according to the invention for the preparationof compounds of the formula (I).

In formula (V), R², R³, X and Y preferably, or in particular, have thosemeanings which have already been mentioned above in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, or as particularly preferred, for R², R³,X and Y;

R⁴ preferably represents methyl, ethyl, phenyl or benzyl.

The starting substances of the formula (V) were hitherto not known fromthe literature and are a subject of the present patent application.

The new 5-alkoxy-1,2,4-triazol-3-(thi)one derivatives of the generalformula (V) are obtained when 5-alkoxy-1,2,4-triazol-3-(thi)ones of thegeneral formula (II) ##STR125## in which R², R³ and Y have theabovementioned meanings are reacted with chloro(thio)formic esters ofthe general formula (IX) ##STR126## in which R⁴ and X have theabovementioned meanings, if appropriate in the presence of a diluentsuch as, for example, tetrahydrofuran, and if appropriate in thepresence of an acid acceptor such as, for example, potassiumtert-butylate, at temperatures between -20° C. and +100° C.

Formula (VI) provides a general definition of the amino compoundsfurthermore to be used as starting substances in process (c) accordingto the invention for the preparation of compounds of the formula (I).

In formula (VI), R¹ preferably, or in particular, has the meaning whichhas already been mentioned above in connection with the description ofthe compounds of the formula (I) according to the invention as beingpreferred, or as particularly preferred, for R¹.

The starting substances of the formula (VI) are known chemicals fororganic synthesis.

Processes (a), (b) and (c) according to the invention for thepreparation of the new compounds of the formula (I) are preferablycarried out in each case using diluents. Suitable diluents for thispurpose are virtually all inert organic solvents. These preferablyinclude aliphatic and aromatic, optionally halogenated hydrocarbons suchas pentane, hexane, heptane, cyclohexane, petroleum ether, benzine,ligroin, benzene, toluene, xylene, methylene chloride, ethylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, ethers such as diethyl ether and dibutyl ether,glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran anddioxane, ketones such as acetone, methyl ethyl ketone, methyl isopropylketone and methyl isobutyl ketone, esters such as methyl acetate andethyl acetate, nitriles such as, for example, acetonitrile andpropionitrile, amides such as, for example, dimethylformamide,dimethylacetamide and N-methyl-pyrrolidone, and also dimethylsulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.

If appropriate, processes (a), (b) and (c) according to the inventionare in each case carried out in the presence of a basic reactionauxiliary. Suitable substances which are employed are preferably basicorganic nitrogen compounds. These include, for example, trimethylamine,triethylamine, tripropylamine, tributylamine, diisopropylamine,dicyclohexylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine,pyridine, 4-dimethylamino-pyridine, 1,5-diazabicyclo-(4,3,0]-non-5-ene(DBN), 1,8-diazabicyclo[5,4,0)-undec-7-ene (DBU) and1,4-diazabicyclo-[2,2,2]-octane (DABCO).

When carrying out processes (a), (b) and (c) according to the invention,the reaction temperatures can be varied in each case in a substantialrange. In general, the processes are carried out at temperatures between-20° C. and 150° C., preferably at temperatures between 0° C. and 100°C.

In general, processes (a), (b) and (c) according to the invention arecarried out under atmospheric pressure. However, it is also possible tocarry out the processes under increased or reduced pressure.

For carrying out processes (a), (b) and (c) according to the invention,the starting substances required in each case are generally employed inapproximately equimolar amounts. However, it is also possible to use oneof the two components employed in each case in a larger excess. Ingeneral, the reactions are carried out in a suitable diluent in thepresence of a basic reaction auxiliary, and the reaction mixture isstirred for several hours at the particular temperature required.Working-up in the processes according to the invention is carried out ineach case by customary methods.

The compounds of the general formula (II) which are used to preparecomponents of formula X in which R² has the abovementioned meaning andR³ represents in each case optionally substituted cycloalkyl,cycloalkenyl, aralkyl or aryl, are new and a subject of the presentpatent application.

The compounds of the formula (II) are obtained when hydrazinoformicesters of the general formula (XV)

    H.sub.2 N--NH--CO--O--R.sup.4.spsp.1                       (XV)

in which

R⁴.spsp.1 has the abovementioned meaning are reacted withalkyliminocarbonic diesters of the general formula (XVI) ##STR127## inwhich R² and R³ have the abovementioned meaning, if appropriate in thepresence of a diluent such as, for example, methanol, at temperaturesbetween 0° C. and 50° C., and the compounds formed in this process, ofthe general formula (XVII) ##STR128## in which R², R³ and R⁴.spsp.1 havethe abovementioned meaning, are, if appropriate, isolated by customarymethods and heated to temperatures between 50° C. and 150° C., ifappropriate in the presence of a diluent such as, for example, toluene,xylene or o-dichlorobenzene (cf. Preparation Examples).

The starting substances of the formulae (XV) and (XVI) are knownchemicals.

The intermediates of the formula (XVII) are new compounds.

Formula (XI) provides a general definition of the sulphonyl isocyanatesfurthermore to be used as starting substances in process (a) accordingto the invention for the preparation of compounds of the formula (X).

In formula (XI), R^(a) preferably, or in particular, has that meaningwhich has already been mentioned above in connection with thedescription of the compounds of the formula (X) according to theinvention as being preferred, or particularly preferred, for R^(a).

Examples of the starting substances of the formula (XI) which may bementioned are: 2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-,2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-,2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsulphinyl-,2-methylsulphonyl-, 2-dimethylaminosulphonyl-, 2-diethylaminosulphonyl-,2-(N-methoxy-N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-,2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and2-isopropoxycarbonyl-phenylsulphonyl isocyanate, 2-fluoro-, 2-chloro-,2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and2-ethoxycarbonyl-benzylsulphonyl isocyanate,2-methoxycarbonyl-3-thienyl-sulphonyl isocyanate, 4-methoxycarbonyl- and4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulphonyl isocyanate.

The sulphonyl isocyanates of the formula (XI) are known and/or can beprepared by processes known per se (cf. U.S. Pat. Nos. 4,127,405,4,169,719, 4,371,391; EP-A 7,687, 13,480, 21,641, 23,141, 23,422,30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041,173,312).

Process (a) according to the invention for the preparation of the newcompounds of the formula (X) is preferably carried out using diluents.Diluents which are suitable for this purpose are virtually all inertorganic solvents. These preferably include aliphatic and aromatic,optionally halogenated hydrocarbons such as pentane, hexane, heptane,cyclohexane, petroleum ether, benzine, ligroine, benzene, toluene,xylene, methylene chloride, ethylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, ethers such asdiethyl ether and dibutyl ether, glycol dimethyl ether and diglycoldimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone,methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone,esters such as methyl acetate and ethyl acetate, nitriles such as, forexample, acetonitrile and propionitrile, amides such as, for example,dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and alsodimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphorictriamide.

When carrying out process (a) according to the invention, the reactiontemperatures can be varied within a substantial range. In general, theprocess is carried out at temperatures between 0° C. and 150° C.,preferably at temperatures between 10° C. and 80° C.

In general, process (a) according to the invention is carried out underatmospheric pressure.

For carrying out process (a) according to the invention, between 1 and 3moles, preferably between 1 and 2 moles, of sulphonyl isocyanate of theformula (XI) are generally employed per mole or triazolinone of theformula (II).

The reactants can be combined in any desired sequence. The reactionmixture is stirred until the reaction is complete and the product isisolated by filtration with suction. In another processing variant, themixture is concentrated, and the crude product which remains in theresidue is brought to crystallisation with a suitable solvent such as,for example, diethyl ether. The product of the formula (X) which isobtained in this way in crystalline form is isolated by filtration withsuction.

Formula (XII) provides a general definition of the triazolinonederivatives to be used as starting substances in process (b) accordingto the invention for the preparation of compounds of the formula (X).

In formula (XII), R² and R³ preferably, or in particular, have thosemeanings which have already been mentioned above in connection withdescription of the compounds of the formula (X) according to theinvention as being preferred, or particularly preferred, for R² and R³and

Z¹ preferably represents chlorine, C₁ -C₄ -alkoxy, benzyloxy or phenoxy,in particular methoxy or phenoxy.

Examples of the starting substances of the formula (XII) which arepossible are the compounds of the formula (XII) which are to be preparedfrom the compounds of the formula (II) listed in Table 3 and phosgene,methyl chloroformate, benzyl chloroformate, phenyl chloroformate ordiphenyl carbonate.

The starting substances of the formula XII were hitherto unknown.

The new triazolinone derivatives of the formula XII are obtained whentriazolinones of the general formula (II) ##STR129## in which R² and R³have the abovementioned meanings are reacted with carbonic acidderivatives of the general formula (XVIII)

    Z.sup.1 --CO--Z.sup.2                                      (XVIII)

in which

Z¹ has the abovementioned meaning and

Z² represents a leaving group such as chlorine, methoxy, benzyloxy orphenoxy,

if appropriate in the presence of a diluent such as, for example,tetrahydrofuran, and, if appropriate, in the presence of an acidacceptor such as, for example, sodium hydride or potassiumtert-butylate, at temperatures between -20° C. and +100° C.

Formula (XVIII) provides a general definition of the sulphonamidesfurthermore to be used as starting substances in process (b) accordingto the invention for the preparation of compounds of the formula (X).

In formula (XIII), R^(a) preferably, or in particular, has that meaningwhich has already been mentioned above in connection with thedescription of the compounds of the formula (X) according to theinvention as being preferred, or particularly preferred, for R^(a).

The following may be mentioned as examples of the starting substances ofthe formula (XIII): 2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-,2-methoxy-, 2-trifluoromethyl-, 2-difluoro-methoxy-,2-trifluoromethoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-,2-methylsulphinyl-, 2-methylsulphonyl-, 2-dimethylaminosulphonyl-,2-diethylaminosulphonyl-, 2-(N-methoxy-N-methyl)-aminosulphonyl-,2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-,2-propoxycarbonyl- and 2-isopropoxycarbonyl-benzenesulphonamide,2-fluoro-, 2-Chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-,2-methoxycarbonyl- and 2-ethoxycarbonyl-phenylmethanesulphonamide,2-methoxycarbonyl-3-thiophenesulphonamide, 4-methoxycarbonyl- and4-ethoxycarbonyl-1-methyl-pyrazole-5-sulphonamide.

The sulphonamides of the formula (XIII) are known and/or can be preparedby processes known per se (cf. U.S. Pat. Nos. 4,127,405, 4,169,719,4,371,391; EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893,44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).

Process (b) according to the invention for the preparation of the newcompounds of the formula (X) is preferably carried out using diluents.Diluents which are suitable for this purpose are virtually all inertorganic solvents as have been indicated, for example, above in the caseof process (a) according to the invention.

Acid acceptors which can be employed in process (b) according to theinvention are all acid-binding agents which can customarily be employedfor reactions of this type. The following are preferably suitable:alkali metal hydroxides such as, for example, sodium hydroxide andpotassium hydroxide, alkaline earth metal hydroxides such as, forexample, calcium hydroxide, alkali metal carbonates and alkali metalalcoholates such as sodium carbonate, potassium carbonate, sodiumtert-butylate and potassium tert-butylate, furthermore aliphatic,aromatic or heterocyclic amines, for example triethylamine,trimethylamine, dimethylaniline, dimethylbenzylamine, pyridine,1,5-diazabicyclo-[4.3.0]-non-5-ene (DBN),1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and1,4-diazabicyclo[2.2.2]-octane (DABCO).

When carrying out process (b) according to the invention, the reactiontemperatures can be varied within a substantial range. In general, theprocess is carried out at temperatures between 0° C. and 100° C.,preferably at temperatures between 10° C. and 60° C.

Process (b) according to the invention is generally carried out underatmospheric pressure. However, it can also be carried out underincreased or reduced pressure.

For carrying out process (b) according to the invention, the startingsubstances required in each case are generally employed in approximatelyequimolar amounts. However, it is also possible to use one of the twocomponents employed in each case in a larger excess. In general, thereactions are carried out in a suitable diluent in the presence of anacid acceptor, and the reaction mixture is stirred for several hours atthe particular temperature required. Working-up in process (b) accordingto the invention is carried out in each case by customary methods.

The triazolinones of the formula (II) to be used as starting substancesin process (c) according to the invention for the preparation ofcompounds of the formula (X) have already been described as startingsubstances for process (a) according to the invention.

Formula (XIV) provides a general definition of the sulphonamidederivatives furthermore to be used as starting substances in process (c)according to the invention for the preparation of compounds of theformula (X).

In formula (XIV), R^(a) and Z¹ preferably, or in particular, have thosemeanings which have already been mentioned above in connection with thedescription of the compounds of the formula (X) or (XII) according tothe invention as being preferred, or particularly preferred, for R^(a)and Z¹.

Process (c) according to the invention is preferably carried out usingdiluents. Solvents which are suitable for this purpose are the sameorganic solvents as have been mentioned above in connection with thedescription of process (a) according to the invention.

If appropriate, process (c) is carried out in the presence of an acidacceptor. Acid-binding agents which are suitable for this purpose arethe same as have been mentioned above in connection with the descriptionof process (b) according to the invention.

When carrying out process (c), the reaction temperatures can vary withina substantial range. In general, the process is carried out attemperatures between 0° C. and 100° C., preferably at temperaturesbetween 10° C. and 60° C.

In general, process (c) according to the invention is carried out underatmospheric pressure. However, the process can also be carried out underincreased or reduced pressure.

For carrying out process (c) according to the invention, the startingsubstances required in each case are generally employed in approximatelyequimolar amounts. However, it is also possible to use one of the twocomponents employed in each case in a larger excess. The reactions aregenerally carried out in a suitable diluent in the presence of an acidacceptor, and the reaction mixture is stirred for several hours at theparticular temperature required. Working-up is carried out in process(c) according to the invention in each case by customary methods.

To convert the compounds of the formula (X) into salts, they are stirredwith suitable salt formers such as, for example, sodium hydroxide,sodium methylate, sodium ethylate, potassium hydroxide, potassiummethylate or potassium ethylate, ammonia, isopropylamine, dibutylamineor triethylamine, in suitable diluents such as, for example, water,methanol or ethanol. The salts can be isolated in the form ofcrystalline products, if appropriate after concentration.

The active compounds according to the invention can be used asdefoliants, desiccants, agents for destroying broad-leaved plants and,especially, as weed-killers. By weeds, in the broadest sense, there areto be understood all plants which grow in locations where they areundesired. Whether the substances according to the invention act astotal or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria,Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio,Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum,Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala,Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis,Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal combating of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for combating weeds in perennialcultures, for example afforestations, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, onlawns, turf and pasture-land, and for the selective combating of weedsin annual cultures.

The compounds of the formula (I) according to the invention are suitablefor selectively combating monocotyledon and dicotyledon weeds, mainly inmonocotyledon cultures, by the pre- and the post-emergence method.

Some of the compounds of the formula (X) according to the invention aresuitable for total or semi-total weed control, some for the selectivecontrol of monocotyledon and dicotyledon weeds in monocotyledon anddicotyledon cultures, both pre-emergence and post-emergence.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surface-active agents, thatis emulsifying agents and/or dispersing agents and/or foam-formingagents.

In the case of the use of water as an extender, organic solvents can,for example, also be used as auxiliary solvents. As liquid solvents,there are suitable in the main: aromatics, such as xylene, toluene, oralkyl-naphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water.

As solid carriers there are suitable: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates, assolid carriers for granules there are suitable: for example crushed andfractionated natural minerals such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,maize cobs and tobacco stalks; as emulsifying and/or foam-forming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumen hydrolysis products; asdispersing agents there are suitable: for example lignin-sulphite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Further additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For combating weeds, the active compounds according to the invention, assuch or in the form of their formulations, can also be used as mixtureswith known herbicides, finished formulations or tank mixes beingpossible.

Suitable herbicides for the mixtures are known herbicides, such as, forexample,1-amino-6-ethylthio-3-(2,2-dimethylpropyl)-1,3,5-triazine-2,4(1H,3H)-dione(AMETHYDIONE) or N-(2-benzothiazolyl)-N,N'-dimethylurea(METABENZTHIAZURON) for combating weeds in cereals;4-amino3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (METAMITRON) forcombating weeds in sugar beet and4-amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazin-(4H) -one(METRIBUZIN) for combating weeds in soya beans; furthermore also2,4-dichlorophenoxyacetic acid (2,4-D); 4-(2,4-dichlorophenoxy)-butyricacid (2,4-DB); 2,4-dichlorophenoxypropionic acid (2,4-DP); 2-chloro-2',6'-diethyl-N-methoxy-methylacetanilide (ALACHLOR);methyl-6,6-dimethyl-2,4-dioxo-3-[1-(2-propenyloxyamino)-butylidene]-cyclohexanecarboxylicacid (ALLOXYDIM); 4-aminobenzenesulphonyl methyl carbamate (ASULAM);2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine (ATRAZINE); methyl2-[[[[[(4,6-dimethoxypyrimidin-2-yl)-amino]carbonyl]-amino]-sulphonyl]-methyl]-benzoate(BENSULFURON); 3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide(BENTAZONE); 3,5-dibromo-4-hydroxy-benzonitrile (BROMOXYNIL);N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)-acetamide (BUTACHLOR);5-amino-4-chloro-2-phenyl-2,3-dihydro-3-oxy-pyridazine (CHLORIDAZONE);isopropyl N-(3-chlorophenyl)-carbamate (CHLORPROPHAM);2-chloro-N-{[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl}-benzenesulphonamide(CHLORSULFURON); N,N-dimethyl-N'-(3-chloro-4-methyl-phenyl)-urea(CHLORTOLURON);exo-1-methyl-4-(1-methyl-ethyl)-2-(2-methylphenyl-methoxy)-7-oxabicyclo-(2,2,1)-heptane(CINMETHYLIN); 3,6-dichloro-2-pyridinecarboxylic acid (CLOPYRALID);2-chloro-4-ethylamino-6-(3-cyanopropylamino)-1,3,5-triazine (CYANAZINE);N,S-diethyl N-cyclohexyl-thiolcarbamate (CYCLOATE);2-[1-(ethoximino)-butyl]-3-hydroxy-5-[tetrahydro-(2H)-thiopyran-3-yl]-2-cyclohexene-1-one(CYCLOXYDIM); 2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid, itsmethyl ester or its ethyl ester (DICLOFOP);2-[(2-chlorophenyl)methyl]-4,4-dimethylisoxazolidin-3-one (DIMETHAZONE);S-ethyl N,N-di-n-propyl-thiocarbamidate (EPTAME);4-amino-6-t-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one (ETHIOZIN);2-{4-[(6-chloro-2-benzoxazolyl)-oxy]phenoxy}-propanoic acid, its methylester or its ethyl ester (FENOXAPROP);2-[4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy]-propanoic acid or itsbutyl ester (FLUAZIFOP);1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4-pyridone (FLURIDONE);[(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)-oxy]-acetic acid or its1-methylheptyl ester (FLUROXYPYR);2-{4-[(3-chloro-5-(trifluoromethyl)-2-pyridinyl)-oxy]-phenoxy}-propanoicacid or its ethyl ester (HALOXYFOP);3-cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4-dione(HEXAZINONE); methyl2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-4(5)-methylbenzoate(IMAZAMETHABENZ); 3,5-diiodo-4-hydroxybenzonitrile (IOXYNIL);N,N-dimethyl-N'-(4-isopropylphenyl)-urea (ISOPROTURON);(2-methyl-4-chlorophenoxy)-acetic acid (MCPA);(4-chloro-2-methylphenoxy)-propionic acid (MCPP);N-methyl-2-(1,3-benzothiazol-2-yloxy)-acetanilide (MEFENACET);2-chloro-N-(2,6-dimethylphenyl)-N-[(1H)-pyrazol-1-yl-methyl]acetamide(METAZACHLOR);2-ethyl-6-methyl-N-(1-methyl-2-methoxyethyl)-chloroacetanilide(METOLACHLOR);2-{[[((4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino)carbonyl]-amino]-sulphonyl}-benzoicacid or its methyl ester (METSULFURON); S-ethylN,N-hexamethylene-thiocarbamate (MOLINATE);1-(3-trifluoromethylphenyl)-4-methylamino-5-chloro-6-pyridazone(NORFLURAZON); 4-(di-n-propyl-amino)-3,5-dinitrobenzenesulphonamide(ORYZALIN); N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline(PENDIMETHALIN);3-(ethoxycarbonylaminophenyl)-N-(3'-methylphenyl)-carbamate(PHENMEDIPHAM); 2-chloro-N-isopropylacetanilide (PROPACHLOR); isopropylN-phenyl-carbamate (PROPHAM); O-(6-chloro-3-phenyl-pyridazin-4-yl)S-octyl thiocarbonate (PYRIDATE); ethyl2-[4-(6-chloroquinoxalin-2-yl-oxy)-phenoxy]-propionate(QUIZALOFOPETHYL);2-[1-(ethoxamino)-butylidene]-5-(2-ethylthiopropyl)-1,3-cyclohexadione(SETHOXYDIM); 2-chloro-4,6-bis-(ethylamino)-1,3,5-triazine (SIMAZINE);2,4-bis-[N-ethylamino]-6-methylthio-1,3,5-triazine (SIMETRYNE);4-ethylamino-2-t-butylamino-6-methylthio-s-triazine (TERBUTRYNE); methyl3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-sulphonyl]-thiophene-2-carboxylate(THIAMETURON); S-[(4-chlorophenyl)-methyl]N,N-diethylthiocarbamate(THIOBENCARB); S-(2,3,3-trichloroallyl) N,N-diisopropylthiocarbamate(TRIALLATE); 2,6-dinitro-4-trifluoromethyl-N,N-dipropylaniline(TRIFLURALIN). Surprisingly, some mixtures also show a synergisticaction.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellants, plant nutrientsand agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomising or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants.

They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 1 g and 10 kg of active compound perhectare of soil surface, preferably between 10 g and 5 kg per ha.

The preparation and use of the active compounds according to theinvention can be seen from the following examples.

PREPARATION EXAMPLES Example 1 ##STR130##

A mixture of 1.3 g (0.01 mol) of5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 0.1 g of1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1.0 g (0.01 mol) of tertbutylisocyanate and 50 ml of acetonitrile is stirred for 12 hours at 20° C.and subsequently concentrated under a water pump vacuum. The residue istaken up in methylene chloride, and the mixture is washed with water,dried with magnesium sulphate and filtered. The filtrate is concentratedunder a water pump vacuum, the residue is brought to crystallisation bytrituration with petroleum ether, and the product is isolated byfiltration with suction.

1.4 g (61% Of theory) of2-tert-butyl-amino-carbonyl-5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 167° C. are obtained.

Other examples of the compounds of the formula (I) which can be preparedanalogously to Example 1 and corresponding to the general description ofthe preparation processes according to the invention are those listed inTable 4 below. ##STR131##

                                      TABLE 4                                     __________________________________________________________________________    Preparation examples of the compounds of the formula (I)                      Example                                           Melting                     No.  R.sup.1                R.sup.2  R.sup.3  X Y point                       __________________________________________________________________________                                                      (°C.)                 2                                                                                                        CH.sub.3 CH.sub.3 O O 153                          3                                                                                  ##STR132##            C.sub.3 H.sub.7                                                                        CH.sub.3 O O (oil)                        4                                                                                  ##STR133##            C.sub.3 H.sub.7                                                                        CH.sub.3 O O (oil)                        5                                                                                  ##STR134##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O (oil)                        6                                                                                  ##STR135##            C.sub.2 H.sub.5                                                                        CH.sub.3 O O (oil)                        7                                                                                  ##STR136##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O (oil)                        8                                                                                  ##STR137##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O (oil)                        9                                                                                  ##STR138##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O (oil)                       10                                                                                  ##STR139##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O (oil)                       11                                                                                  ##STR140##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O (oil)                       12                                                                                  ##STR141##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O (oil)                       13                                                                                  ##STR142##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O (oil)                       14                                                                                  ##STR143##            CH.sub.3 CH.sub.3 O O 166                         15                                                                                  ##STR144##            CH.sub.3 CH.sub.3 O O 120                         16                                                                                  ##STR145##            CH.sub.3 CH.sub.3 O O 176                         17                                                                                  ##STR146##            CH.sub.3 CH.sub.3 O O 130                         18                                                                                  ##STR147##            CH.sub.3 CH.sub.3 O O 104                         19                                                                                  ##STR148##            CH.sub.3 CH.sub.3 O O 117                         20                                                                                  ##STR149##            CH.sub.3 CH.sub.3 O O 100                         21   (CH.sub.3).sub.3 C     CH.sub.3 C.sub.3 H.sub.7                                                                        O O  75                         22                                                                                  ##STR150##            CH.sub.3 C.sub.3 H.sub.7                                                                        O O  95                         23                                                                                  ##STR151##            CH.sub.3 CH.sub.3 O O 142                         24                                                                                  ##STR152##            CH.sub.3 CH.sub.3 O O 135                         25                                                                                  ##STR153##            CH.sub.3 CH.sub.3 O O 106                         26                                                                                  ##STR154##            CH.sub.3 CH.sub.3 O O 137                         27                                                                                  ##STR155##            CH.sub.3 CH.sub.3 O O 131                         28                                                                                  ##STR156##            CH.sub.3 CH.sub.3 O O 118                         29                                                                                  ##STR157##            CH.sub.3 CH.sub.3 O O  82                         30   (CH.sub.3).sub.3 C     CH.sub.2 CHCH.sub.2                                                                    CH.sub.3 O O  87                         31   (CH.sub.3).sub.3 C     n-C.sub.3 H.sub.7                                                                      CH.sub.3 O O 144                         32   (CH.sub.3).sub.3 C     CH.sub.3 C.sub.2 H.sub.5                                                                        O O 102-103                     33   (CH.sub.3).sub.3 C     CH.sub.3 C.sub.4 H.sub.9 -n                                                                     O O 79-80                       34   (CH.sub.3).sub.3 C                                                                                    ##STR158##                                                                            C.sub.2 H.sub.5                                                                        O O 108                         35   (CH.sub.3).sub.3 C     C.sub.2 H.sub.5                                                                        CH.sub.3 O O 144-146                     36   (CH.sub.3).sub.3 C     CH.sub.2 CHCH.sub.2                                                                    C.sub.2 H.sub.5                                                                        O O 63-64                       37   (CH.sub.3).sub.3 C     i-C.sub.3 H.sub.7                                                                      C.sub.2 H.sub.5                                                                        O O 68-69                       38   (CH.sub.3).sub.3 C     (CH.sub.2).sub.3 OCH.sub.3                                                             CH.sub.3 O O 86-87                       39   (CH.sub.3).sub.3 C     n-C.sub.3 H.sub.7                                                                      C.sub.2 H.sub.5                                                                        O O 70-71                       40                                                                                  ##STR159##            CH.sub.3 C.sub.4 H.sub.9 -n                                                                     O O Oil                         41                                                                                  ##STR160##                                                                                           ##STR161##                                                                            C.sub.2 H.sub.5                                                                        O O Oil                         42                                                                                  ##STR162##            C.sub.2 H.sub.5                                                                        CH.sub.3 O O Oil                         43                                                                                  ##STR163##            CH.sub.3 i-C.sub.3 H.sub.7                                                                      O O Oil                         44                                                                                  ##STR164##            n-C.sub.3 H.sub.7                                                                      CH.sub.3 O O  78                         45                                                                                  ##STR165##            CH.sub.2 CHCH.sub.2                                                                    C.sub.2 H.sub.5                                                                        O O Oil                         46                                                                                  ##STR166##            n-C.sub.3 H.sub.7                                                                      CH.sub.3 O O 93-94                       47                                                                                  ##STR167##            CH.sub.3 C.sub.4 H.sub.9 -n                                                                     O O Oil                         48                                                                                  ##STR168##                                                                                           ##STR169##                                                                            C.sub.2 H.sub.5                                                                        O O Oil                         49                                                                                  ##STR170##            C.sub.2 H.sub.5                                                                        CH.sub.3 O O Oil                         50                                                                                  ##STR171##            CH.sub.2 CHCH.sub.2                                                                    C.sub.2 H.sub.5                                                                        O O Oil                         51                                                                                  ##STR172##            i-C.sub.3 H.sub.7                                                                      C.sub.2 H.sub.5                                                                        O O Oil                         52                                                                                  ##STR173##            (CH.sub.2).sub.3 OCH.sub.3                                                             CH.sub.3 O O 104-105                     53                                                                                  ##STR174##            n-C.sub.3 H.sub.7                                                                      C.sub.2 H.sub.5                                                                        0 0 Oil                         54                                                                                  ##STR175##            i-C.sub.3 H.sub.7                                                                      CH.sub.3 O O Oil                         55                                                                                  ##STR176##            CH.sub.3 i-C.sub.3 H.sub.7                                                                      O O Oil                         56                                                                                  ##STR177##            n-C.sub.3 H.sub.7                                                                      CH.sub.3 O O Oil                         57                                                                                  ##STR178##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O Oil                         58                                                                                  ##STR179##            C.sub.2 H.sub.5                                                                        CH.sub.3 O O Oil                         59                                                                                  ##STR180##            CH.sub.2 CHCH.sub.2                                                                    C.sub.2 H.sub.5                                                                        O O Oil                         60                                                                                  ##STR181##            n-C.sub.3 H.sub.7                                                                      C.sub.2 H.sub.5                                                                        O O Oil                         61                                                                                  ##STR182##            i-C.sub.3 H.sub.7                                                                      CH.sub.3 O O Oil                         62                                                                                  ##STR183##            CH.sub.3 i-C.sub.3 H.sub.7                                                                      O O Oil                         63                                                                                  ##STR184##            n-C.sub.3 H.sub.7                                                                      CH.sub.3 O O Oil                         64                                                                                  ##STR185##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O Oil                         65                                                                                  ##STR186##            CH.sub.3 n-C.sub.4 H.sub.9                                                                      O O Oil                         66                                                                                  ##STR187##            C.sub.2 H.sub.5                                                                        CH.sub.3 O O Oil                         67                                                                                  ##STR188##            n-C.sub.3 H.sub.7                                                                      C.sub.2 H.sub.5                                                                        O O Oil                         68                                                                                  ##STR189##            i-C.sub.3 H.sub.7                                                                      CH.sub.3 O O Oil                         69                                                                                  ##STR190##            n-C.sub.3 H.sub.7                                                                      CH.sub.3 O O Oil                         70                                                                                  ##STR191##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O Oil                         71                                                                                  ##STR192##            CH.sub.3 n-C.sub.4 H.sub.9                                                                      O O Oil                         72                                                                                  ##STR193##            C.sub.2 H.sub.5                                                                        CH.sub.3 O O Oil                         73                                                                                  ##STR194##            n-C.sub.3 H.sub.7                                                                      C.sub.2 H.sub.5                                                                        O O Oil                         74                                                                                  ##STR195##            n-C.sub.3 H.sub.7                                                                      CH.sub.3 O O Oil                         75                                                                                  ##STR196##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O Oil                         76                                                                                  ##STR197##            C.sub.2 H.sub.5                                                                        CH.sub.3 O O Oil                         77                                                                                  ##STR198##            CH.sub.2 CHCH.sub.2                                                                    C.sub.2 H.sub.5                                                                        O O Oil                         78                                                                                  ##STR199##            n-C.sub.3 H.sub.7                                                                      C.sub.2 H.sub.5                                                                        O O Oil                         79                                                                                  ##STR200##            n-C.sub.3 H.sub.7                                                                      CH.sub.3 O O 107-108                     80                                                                                  ##STR201##            CH.sub.3 C.sub.4 H.sub.9 -n                                                                     O O Oil                         81                                                                                  ##STR202##            C.sub.2 H.sub.5                                                                        CH.sub.3 O O 83-85                       82                                                                                  ##STR203##            n-C.sub.3 H.sub.7                                                                      C.sub.2 H.sub.5                                                                        O O 125-127                     83                                                                                  ##STR204##            i-C.sub.3 H.sub.7                                                                      CH.sub.3 O O 108-110                     84                                                                                  ##STR205##            n-C.sub.3 H.sub.7                                                                      CH.sub.3 O O 100-102                     85                                                                                  ##STR206##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O 164-166                     86                                                                                  ##STR207##            CH.sub.3 n-C.sub.4 H.sub.9                                                                      O O 145                         87                                                                                  ##STR208##            n-C.sub.3 H.sub.7                                                                      CH.sub.3 O O 109-110                     88                                                                                  ##STR209##                                                                                           ##STR210##                                                                            C.sub.2 H.sub.5                                                                        O O 123-125                     89                                                                                  ##STR211##            n-C.sub.3 H.sub.7                                                                      C.sub.2 H.sub.5                                                                        O O 95-98                       90                                                                                  ##STR212##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O 90-91                       91                                                                                  ##STR213##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O 64-66                       92                                                                                  ##STR214##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O 84-85                       93                                                                                  ##STR215##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O 104-105                     94                                                                                  ##STR216##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O 113-116                     95                                                                                  ##STR217##                                                                                           ##STR218##                                                                            C.sub.2 H.sub.5                                                                        O O  95                         96                                                                                  ##STR219##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O 115-116                     97   (CH.sub.3).sub.3 C     CH.sub.3 i-C.sub.3 H.sub.7                                                                      O O 82-84                       98   ClCH.sub.2 C(CH.sub.3).sub.2                                                                         n-C.sub.3 H.sub.7                                                                      CH.sub.3 O O 93-95                       99   ClCH.sub.2 C(CH.sub.3).sub.2                                                                         CH.sub.3 n-C.sub.4 H.sub.9                                                                      O O 85-87                       100  ClCH.sub.2 C(CH.sub.3).sub.2                                                                         C.sub.2 H.sub.5                                                                        CH.sub.3 O O 127-129                     101  ClCH.sub.2 C(CH.sub.3).sub.2                                                                         CH.sub.2 CHCH.sub.2                                                                    C.sub.2 H.sub.5                                                                        O O Oil                         102  ClCH.sub.2 C(CH.sub.3).sub.2                                                                         n-C.sub.3 H.sub.7                                                                      C.sub.2 H.sub.5                                                                        O O 63-65                       103  ClCH.sub.2 C(CH.sub.3).sub.2                                                                         CH.sub.3 i-C.sub.3 H.sub.7                                                                      O O 85-87                       104  ClCH.sub.2 C(CH.sub.3).sub.2                                                                         CH.sub.3 C.sub.2 H.sub.5                                                                        O O 95-96                       105                                                                                 ##STR220##            CH.sub.3 i-C.sub.3 H.sub.7                                                                      O O 146                         106                                                                                 ##STR221##            CH.sub.3 i-C.sub.3 H.sub.7                                                                      O O Oil                         107                                                                                 ##STR222##            CH.sub.3 i-C.sub.3 H.sub.7                                                                      O O Oil                         108                                                                                 ##STR223##            CH.sub.3 i-C.sub.3 H.sub.7                                                                      O O Oil                         109                                                                                 ##STR224##            CH.sub.3 C.sub.2 H.sub.5                                                                        O O 115-117                     110                                                                                 ##STR225##            C.sub.2 H.sub.5                                                                        CH.sub.3 O O 129-130                     111                                                                                 ##STR226##                                                                                           ##STR227##                                                                            C.sub.2 H.sub.5                                                                        O O Oil                         112  (CH.sub.3).sub.3 C     CH.sub.3 (CH.sub.2).sub.2 OC.sub.2 H.sub.5                                                      O O  58                         113  ClCH.sub.2 C(CH.sub.3).sub.2                                                                         CH.sub.3 (CH.sub.2).sub.2 OC.sub.2 H.sub.5                                                      O O Oil                         114                                                                                 ##STR228##            CH.sub.3 (CH.sub.2).sub.2 OC.sub.2 H.sub.5                                                      O O 126-128                     115                                                                                 ##STR229##            CH.sub.3 (CH.sub.2).sub.2 OC.sub.2 H.sub.5                                                      O O Oil                         116                                                                                 ##STR230##            CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3                                                             O O Oil                         117                                                                                 ##STR231##            CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3                                                             O O Oil                         118                                                                                 ##STR232##            CH.sub.3 CH.sub.3 O O  83                         119                                                                                 ##STR233##            CH.sub.3 CH.sub.3 O O 169                         120                                                                                 ##STR234##            CH.sub.3 CH.sub.3 O O 117                         121  (CH.sub.3).sub.2 CHCH.sub.2                                                                          CH.sub.3 CH.sub.3 O O 120                         122                                                                                 ##STR235##            CH.sub.3 CH.sub.3 O O 171                         123  n-C.sub.3 H.sub.7 C(CH.sub.3).sub.2                                                                  CH.sub.3 CH.sub.3 O O 147                         124                                                                                 ##STR236##            CH.sub.3 CH.sub.3 O O 139                         125                                                                                 ##STR237##            CH.sub.3 CH.sub.3 O O 165                         126  CH.sub.3 C(C.sub.2 H.sub.5).sub.2                                                                    CH.sub.3 CH.sub.3 O O 149                         127                                                                                 ##STR238##            CH.sub.3 CH.sub.3 O O  92                         128                                                                                 ##STR239##            CH.sub.3 CH.sub.3 O O 105                         129                                                                                 ##STR240##            CH.sub.3 CH.sub.3 O O 104                         130                                                                                 ##STR241##            CH.sub.3 CH.sub.3 O O 182                         131                                                                                 ##STR242##            CH.sub.3 CH.sub.3 O O  61                         132  (C.sub.2 H.sub.5).sub.3 C                                                                            CH.sub.3 CH.sub.3 O O 148                         133  C.sub.2 H.sub.5 C(CH.sub.3).sub.2                                                                    CH.sub.3 CH.sub.3 O O 151                         134                                                                                 ##STR243##            CH.sub.3 CH.sub.3 O O 126                         135                                                                                 ##STR244##            CH.sub.3 CH.sub.3 O O 128                         136                                                                                 ##STR245##            CH.sub.3 CH.sub.3 O O 146                         137  n-C.sub.6 H.sub.13     CH.sub.3 CH.sub.3 O O 110                         138  (CH.sub.3).sub.3 CCH.sub.2 C(CH.sub.3).sub.2                                                         CH.sub.3 CH.sub.3 O O 150                         139                                                                                 ##STR246##            CH.sub.3 CH.sub.3 O O 126                         140  HCCC(CH.sub.3).sub.2   CH.sub.3 CH.sub.3 O O 198                         141                                                                                 ##STR247##            CH.sub.3 CH.sub.3 O O 165                         142                                                                                 ##STR248##            CH.sub.3 CH.sub.3 O O 154                         143  (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2                                                                 CH.sub.3 CH.sub.3 O O 135                         144  (CH.sub.3).sub.2 CHC(CH.sub.3).sub.2                                                                 CH.sub.3 CH.sub.3 O O 158                         145  Cl.sub.2 CHC(CH.sub.3).sub.2                                                                         CH.sub.3 CH.sub.3 O O 153                         146                                                                                 ##STR249##            CH.sub.3 CH.sub.3 O O 129                         147  n-C.sub.5 H.sub.11     CH.sub.3 CH.sub.3 O O 107                         148  (C.sub.2 H.sub.5).sub.2 CHCH.sub.2                                                                   CH.sub.3 CH.sub.3 O O  91                         149                                                                                 ##STR250##            CH.sub.3 CH.sub.3 O O  85                         150  (CH.sub.3).sub.2 CH    CH.sub.3 CH.sub.3 O O 118                         151  (ClCH.sub.2).sub.2 C(CH.sub.3)                                                                       CH.sub.3 CH.sub.3 O O 153                         152  FCH.sub.2 C(CH.sub.3).sub.2                                                                          CH.sub.3 CH.sub.3 O O 151                         153                                                                                 ##STR251##            CH.sub.3 CH.sub.3 O O 123                         154                                                                                 ##STR252##            CH.sub.3 CH.sub.3 O O  91                         155                                                                                 ##STR253##            CH.sub.3 CH.sub.3 O O 173                         156                                                                                 ##STR254##            CH.sub.3 CH.sub.3 O O 149                         157                                                                                 ##STR255##            CH.sub.3 CH.sub.3 O O 147                         158                                                                                 ##STR256##            CH.sub.3 CH.sub.3 O O  87                         159                                                                                 ##STR257##            CH.sub.3 CH.sub.3 O O 162                         160                                                                                 ##STR258##            CH.sub.3 CH.sub.3 O O  60                         161  n-C.sub.3 H.sub.7      CH.sub.3 CH.sub.3 O O 107                         162                                                                                 ##STR259##            CH.sub.3 CH.sub.3 O O 131                         163  ClCH.sub.2 CH.sub.2    CH.sub.3 CH.sub.3 O O 117                         164                                                                                 ##STR260##            CH.sub.3 CH.sub.3 O O  96                         165                                                                                 ##STR261##            CH.sub.3 CH.sub.3 O O  86                         166                                                                                 ##STR262##            CH.sub.3 CH.sub.3 O O  85                         167                                                                                 ##STR263##            CH.sub.3 CH.sub.3 O O  90                         168                                                                                 ##STR264##            CH.sub.3 CH.sub.3 O O 107                         169                                                                                 ##STR265##            CH.sub.3 CH.sub.3 O O  94                         170                                                                                 ##STR266##            CH.sub.3 CH.sub.3 O O 122                         171                                                                                 ##STR267##            CH.sub.3 CH.sub.3 O O 137                         172                                                                                 ##STR268##            CH.sub.3 CH.sub.3 O O 139                         173                                                                                 ##STR269##            CH.sub.3 CH.sub.3 O O  91                         174                                                                                 ##STR270##            CH.sub.3 CH.sub.3 O O  59                         __________________________________________________________________________

PREPARATION EXAMPLES OF COMPOUNDS OF FORMULA X Example 175 ##STR271##(Process (a))

A mixture of 2.0 g (10.5 mmol) of4-methyl-5-phenoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, 3.5 g (14.5 mmol)of 2-methoxycarbonyl-phenylsulphonyl isocyanate and 60 ml ofacetonitrile is stirred for 6 hours at 20° C. and subsequentlyconcentrated under a water pump vacuum. The residue is stirred withdiethyl ether and the product which has precipitated in crystalline formis isolated by filtration with suction.

4.1 g (90% of theory) of2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-phenoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 161° C. are obtained.

Other examples of compounds of the formula (X) which can be preparedanalogously to Example 175 and following the general description of thepreparation processes according to the invention are those listed inTable 5 below. ##STR272##

                                      TABLE 5                                     __________________________________________________________________________    Preparation Examples of the compounds of the                                  formula (X)                                                                   Example                                Melting                                No.  R.sup.2   R.sup.3     R.sup.a     point (°C.)                     __________________________________________________________________________    176                                                                                          C.sub.2 H.sub.5                                                                            ##STR273## 183                                    177  CH.sub.3                                                                                 ##STR274##                                                                                ##STR275## 190                                    178  CH.sub.3  C.sub.3 H.sub.7                                                                            ##STR276## 120                                    179  CH.sub.3  C.sub.3 H.sub.7                                                                            ##STR277## 134                                    180  CH.sub.3  C.sub.3 H.sub.7                                                                            ##STR278## 122                                    181  CH.sub.3  C.sub.3 H.sub.7                                                                            ##STR279## 125                                    182  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR280## 166-167                                183  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR281## 131-132                                184  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR282## 147-148                                185  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR283## 186-187                                186  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR284## 125-126                                187  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR285## 123-124                                188  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR286## 188-189                                189  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR287## 175-176                                190  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR288## 152-153                                191  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR289## 172-173                                192  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR290## 147-148                                193  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR291## 183-184                                194  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR292## 178-183                                195  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR293## 155-156                                196  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR294## 162-163                                197  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR295## 146-147                                198  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR296## 129-130                                199  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR297## 150-151                                200  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR298## 130-131                                201  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR299## 135-136                                202  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR300## 126-127                                203  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR301## 116-117                                204  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR302## 129-130                                205  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR303## 156-157                                206  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR304## 117-118                                207  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR305## 139-140                                208  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR306## 115-116                                209  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR307## 183-184                                210  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR308## 130-131                                211  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR309## 108-109                                212  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR310## 122-123                                213  C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                   ##STR311## 128-129                                214  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR312##  76                                    215  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR313## 197                                    216  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR314## 153                                    217  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR315## 105                                    218  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR316##  81                                    219  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR317## 137                                    220  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR318## 148                                    221  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR319## 114                                    222  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR320## 147                                    223  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR321## 139                                    224                                                                                 ##STR322##                                                                             C.sub.2 H.sub.5                                                                            ##STR323## 114                                    225                                                                                 ##STR324##                                                                             C.sub.2 H.sub.5                                                                            ##STR325## 135                                    226                                                                                 ##STR326##                                                                             C.sub.2 H.sub.5                                                                            ##STR327## 108                                    227  CH.sub.3                                                                                 ##STR328##                                                                                ##STR329## 209                                    228  CH.sub.3                                                                                 ##STR330##                                                                                ##STR331## 191                                    229  CH.sub.3                                                                                 ##STR332##                                                                                ##STR333## 207                                    230  CH.sub.3  CH.sub.3                                                                                   ##STR334## 154                                    231  CH.sub.3  CH.sub.3                                                                                   ##STR335## 187                                    232  CH.sub.3  CH.sub.3                                                                                   ##STR336## 179                                    233  CH.sub.2 CHCH.sub.2                                                                     CH.sub.3                                                                                   ##STR337## 124                                    234  CH.sub.2 CHCH.sub.2                                                                     CH.sub.3                                                                                   ##STR338## 153                                    235  CH.sub.2 CHCH.sub.2                                                                     CH.sub.3                                                                                   ##STR339## 150                                    236  CH.sub.2 CHCH.sub.2                                                                     CH.sub.3                                                                                   ##STR340## 103                                    237  CH.sub.2 CHCH.sub.2                                                                     CH.sub.3                                                                                   ##STR341## 130                                    238  CH.sub.3  CH.sub.3                                                                                   ##STR342## 196                                    239  CH.sub.3  CH.sub.3                                                                                   ##STR343## 136                                    240  CH.sub.2 CHCH.sub.2                                                                     CH.sub.3                                                                                   ##STR344## 130                                    241  CH.sub.3                                                                                 ##STR345##                                                                                ##STR346## 211                                    242  CH.sub.3                                                                                 ##STR347##                                                                                ##STR348## 179                                    243  CH.sub.3  CH.sub.3                                                                                   ##STR349## 171                                    244  CH.sub.2 CHCH.sub.2                                                                     CH.sub.3                                                                                   ##STR350## 115                                    245  CH.sub.3                                                                                 ##STR351##                                                                                ##STR352## 162                                    246  CH.sub.3  C.sub.3 H.sub.7                                                                            ##STR353## 141                                    247  CH.sub.3  CH.sub.3                                                                                   ##STR354## 148                                    248  CH.sub.3                                                                                 ##STR355##                                                                                ##STR356## 174                                    249  CH.sub.2 CHCH.sub.2                                                                     CH.sub.3                                                                                   ##STR357## 138                                    250                                                                                 ##STR358##                                                                             CH.sub.3                                                                                   ##STR359## 148                                    251                                                                                 ##STR360##                                                                             CH.sub.3                                                                                   ##STR361## 150                                    252  CH.sub.2 CHCH.sub.2                                                                     CH.sub.3                                                                                   ##STR362## 125                                    253  CH.sub.3  CH.sub.3                                                                                   ##STR363## 145                                    254  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR364## 153-154                                255  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR365## 151-152                                256  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR366## 167-168                                257  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR367## 155-156                                258  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR368## 174-175                                259  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR369## 140-141                                260  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR370## 160                                    261  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR371## 146-147                                262  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR372## 156-157                                263  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR373## 125-126                                264  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR374## 137-138                                265  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR375## 203-204                                266  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR376## 118-119                                267  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR377## 146-147                                268  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR378## 110-111                                269  CH.sub.3  C.sub.4 H.sub.9                                                                            ##STR379## 123-124                                270                                                                                 ##STR380##                                                                             C.sub.2 H.sub.5                                                                            ##STR381## 152-153                                271                                                                                 ##STR382##                                                                             C.sub.2 H.sub.5                                                                            ##STR383## 116-117                                272                                                                                 ##STR384##                                                                             C.sub.2 H.sub.5                                                                            ##STR385## 145-146                                273                                                                                 ##STR386##                                                                             C.sub.2 H.sub.5                                                                            ##STR387## 132-133                                274                                                                                 ##STR388##                                                                             C.sub.2 H.sub.5                                                                            ##STR389## 88-89                                  275                                                                                 ##STR390##                                                                             C.sub.2 H.sub.5                                                                            ##STR391## 128-129                                276                                                                                 ##STR392##                                                                             C.sub.2 H.sub.5                                                                            ##STR393## 79-77                                  277  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR394## 114-115                                278  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR395## 104-106                                279  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR396## 85-86                                  280  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR397## 121-122                                281  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR398## 107-108                                282  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR399## 123-124                                283  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR400## 131-132                                284  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR401## 118-119                                285  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR402## 110-111                                286  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR403## 123-124                                287  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR404## 103-104                                288  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR405## >250                                   289  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR406## 114-115                                290  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR407## 122-123                                291  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                            ##STR408## 188-190                                292  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                            ##STR409## 230-231                                293  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                            ##STR410## 129-130                                294  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                            ##STR411## 207 (Zers.)                            295  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                            ##STR412## 113-114                                296  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                            ##STR413## 195-200                                297  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                            ##STR414## 133-134                                298  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                            ##STR415## 139-140                                299  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                            ##STR416## 105-106                                300  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                            ##STR417## 123-124                                301  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                                   ##STR418## 112-114                                302  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                                   ##STR419## 92-95                                  303  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                                   ##STR420## 126-127                                304  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                                   ##STR421## 115-116                                305  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                                   ##STR422## 112-113                                306  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                                   ##STR423## 81-82                                  307  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                                   ##STR424## 104-105                                308  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                                   ##STR425## 113-114                                309  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                                   ##STR426## 91-92                                  310  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR427## 108 (Zers.)                            311  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR428## 212-213                                312  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR429## 106-107                                313  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR430## 127-128                                314  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR431##  95 (Zers.)                            315  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR432## 132-135                                316  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR433## 138-140                                317  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR434## 87-88                                  318  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR435## 108-109                                319  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR436## 154-157                                320  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR437## 130-133                                321  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR438## 150-151                                322  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR439## 160-161                                323  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR440## 147-148                                324  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR441## 148-150                                324  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR442## 143-144                                326  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR443## 134-135                                327  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR444## 147-150                                328  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR445## 148-150                                329  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR446## 143-145                                330  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR447## 114-116                                331  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR448## 125-128                                332  CH.sub.3  CH(CH.sub.3).sub.2                                                                         ##STR449## 95-97                                  333  CH.sub.3  CH(CH.sub.3).sub.2                                                                         ##STR450## 158-160                                334  CH.sub.3  CH(CH.sub.3).sub.2                                                                         ##STR451## 152-153                                335  CH.sub.3  CH(CH.sub.3).sub.2                                                                         ##STR452## 150-152                                336  CH.sub.3  CH(CH.sub.3).sub.2                                                                         ##STR453## 128-130                                337  CH.sub.3  CH(CH.sub.3).sub.2                                                                         ##STR454## 150-152                                338  CH.sub.3                                                                                 ##STR455##                                                                                ##STR456## 117-118                                339  CH.sub.3                                                                                 ##STR457##                                                                                ##STR458## 130-132                                340                                                                                 ##STR459##                                                                             C.sub.2 H.sub.5                                                                            ##STR460## 148-150                                341  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR461## 172-173                                342  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR462## 130-132                                343  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                            ##STR463## 142-144                                344  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                                   ##STR464## 127-130                                345  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR465## 127-130                                346  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR466## 156-157                                347  CH.sub.3  CH(CH.sub.3).sub.2                                                                         ##STR467## 198-200                                348  CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                            ##STR468## 122-124                                349  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                                   ##STR469## 97-98                                  350  n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                            ##STR470## 128-130                                351  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                   ##STR471## 148-150                                352  CH.sub.3  CH(CH.sub.3).sub.2                                                                         ##STR472## 154                                    353  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR473## 145                                    354  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR474## 134-136                                355  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR475## 178                                    356  CH.sub.3  n-C.sub.4 H.sub.9                                                                          ##STR476## 142-143                                357  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR477## 115-118                                358  CH.sub.2 CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                            ##STR478## 98-99                                  359  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR479## 114-115 (Na-Salz)                      360  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR480## 135-140 (Na-Salz)                      361  CH.sub.3  CH.sub.3                                                                                   ##STR481## 161-163 (Na-Salz)                      362  CH.sub.3  C.sub.6 H.sub.5                                                                            ##STR482## 185                                    363  CH.sub.3  C.sub.6 H.sub.5                                                                            ##STR483## 202                                    364  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR484## 160 (sodium salt)                      365  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR485## 144 (sodium salt)                      366  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                   ##STR486## 180 (sodium salt)                      367  CH.sub.3  n-C.sub.4 H.sub.9                                                                          ##STR487## >270  (sodium salt)                    368  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR488## 124 (sodium salt)                      369  CH.sub.3  i-C.sub.3 H.sub.7                                                                          ##STR489## 160                                    370  CH.sub.3  i-C.sub.3 H.sub.7                                                                          ##STR490## 167                                    371  CH.sub.3  i-C.sub.3 H.sub.7                                                                          ##STR491## 166                                    372  CH.sub.3  i-C.sub.3 H.sub.7                                                                          ##STR492## 145                                    373  CH.sub.3  i-C.sub.3 H.sub.7                                                                          ##STR493## 126                                    374  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR494## 113                                    375  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR495## 102                                    376  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR496## 103                                    377  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR497## 114                                    378  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR498## 105                                    379  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR499## 135                                    380  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR500## 147                                    381  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR501## 127                                    382  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR502## 130                                    383  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR503## 137                                    384  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR504## 127                                    385  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR505## 155                                    386  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR506## 150                                    387  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR507## 120                                    388  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR508## 109                                    389  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR509## 146                                    390  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR510## 150                                    391  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR511## 170                                    392  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR512## 148                                    393  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR513## 130                                    394  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR514## 110                                    395  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR515## 164                                    396  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR516## 122                                    397  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR517##  92                                    398  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR518##  98                                    399  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR519##  76                                    400  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR520##  88                                    401  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR521##  84                                    402  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR522##  80                                    403  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR523##  76                                    404  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR524## 123                                    405  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR525## 122                                    406  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR526## 129                                    407  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR527## 132                                    408  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR528## 122                                    409  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR529##  87                                    410  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR530##  78                                    411  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR531## 106                                    412  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR532##  75                                    413  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR533##  80                                    414  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR534##  78                                    415  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR535##  74                                    416  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR536##  78                                    417  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR537##  68                                    418  C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  ##STR538##  98                                    419  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                        ##STR539##  88                                    420  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                        ##STR540##  98                                    421  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                        ##STR541## 106                                    422  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                        ##STR542## 106                                    423  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                        ##STR543##  92                                    424  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                        ##STR544## 136                                    425  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                        ##STR545## 123                                    426  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                        ##STR546## 122                                    427  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                        ##STR547## 116                                    428  CH.sub.3                                                                                 ##STR548##                                                                                ##STR549##  78                                    429  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                        ##STR550## 126                                    430  CH.sub.3                                                                                 ##STR551##                                                                                ##STR552## 114                                    431  CH.sub.3                                                                                 ##STR553##                                                                                ##STR554## 106                                    432  CH.sub.3                                                                                 ##STR555##                                                                                ##STR556## 107                                    433  CH.sub.3  i-C.sub.3 H.sub.7                                                                          ##STR557## 145                                    434  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR558## 140 (sodium salt)                      435  CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR559## 140 (sodium salt)                      436  CH.sub.3                                                                                 ##STR560##                                                                                ##STR561## 100                                    437  CH.sub.3                                                                                 ##STR562##                                                                                ##STR563##  99                                    438  CH.sub.3                                                                                 ##STR564##                                                                                ##STR565##  86                                    439  CH.sub.3                                                                                 ##STR566##                                                                                ##STR567## 119                                    440  CH.sub.3                                                                                 ##STR568##                                                                                ##STR569## 119                                    441  CH.sub.3                                                                                 ##STR570##                                                                                ##STR571##  93                                    442  CH.sub.3                                                                                 ##STR572##                                                                                ##STR573## 111                                    443  CH.sub.3                                                                                 ##STR574##                                                                                ##STR575## 113                                    444  CH.sub.3                                                                                 ##STR576##                                                                                ##STR577##  86                                    445  CH.sub.3                                                                                 ##STR578##                                                                                ##STR579## 175                                    446  CH.sub.3                                                                                 ##STR580##                                                                                ##STR581##  90                                    447  CH.sub.3                                                                                 ##STR582##                                                                                ##STR583##  95                                    448  CH.sub.3                                                                                 ##STR584##                                                                                ##STR585##  95                                    449  CH.sub.3                                                                                 ##STR586##                                                                                ##STR587## 130                                    450  CH.sub.3                                                                                 ##STR588##                                                                                ##STR589##  77                                    451  CH.sub.3                                                                                 ##STR590##                                                                                ##STR591##  80                                    452  CH.sub.3                                                                                 ##STR592##                                                                                ##STR593##  92                                    453  CH.sub.3                                                                                 ##STR594##                                                                                ##STR595##  74                                    454  CH.sub.3                                                                                 ##STR596##                                                                                ##STR597## 108                                    455  CH.sub.3                                                                                 ##STR598##                                                                                ##STR599## 112                                    456  CH.sub.3                                                                                 ##STR600##                                                                                ##STR601## 103                                    457  CH.sub.3  CH.sub.3                                                                                   ##STR602## 127                                    458  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR603## 123                                    459                                                                                 ##STR604##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR605## 128                                    460  CH.sub.3  CH.sub.3                                                                                   ##STR606## 179                                    461  CH.sub.3  CH.sub.3                                                                                   ##STR607## 176                                    462  CH.sub.3  CH.sub.3                                                                                   ##STR608## 178                                    463  CH.sub.3  CH.sub.3                                                                                   ##STR609## 177                                    464                                                                                 ##STR610##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR611##  94                                    465                                                                                 ##STR612##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR613## 115                                    466                                                                                 ##STR614##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR615## 115                                    467                                                                                 ##STR616##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR617## 119                                    468  CH.sub.3  CH.sub.3                                                                                   ##STR618## 170 (sodium salt)                      469  CH.sub.3  CH.sub.3                                                                                   ##STR619## 166                                    470  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR620## 124                                    471  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR621## 178 (sodium salt)                      472  CH.sub.3  CH.sub.3                                                                                   ##STR622## 192                                    473  CH.sub.3  CH.sub.3                                                                                   ##STR623## 160                                    474  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR624## 149                                    475  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR625## 131                                    476  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR626## 156                                    477  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR627## 131                                    478  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR628## 150                                    479  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR629## 171                                    480  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR630## 147                                    481  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR631## 111                                    482  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR632## 124                                    483  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR633## 112                                    484                                                                                 ##STR634##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR635## 118                                    485                                                                                 ##STR636##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR637## 116                                    486                                                                                 ##STR638##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR639## 103                                    487                                                                                 ##STR640##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR641##  81                                    488                                                                                 ##STR642##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR643## 114                                    489                                                                                 ##STR644##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR645## 120                                    490                                                                                 ##STR646##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR647## 107                                    491                                                                                 ##STR648##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR649## 143                                    492                                                                                 ##STR650##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR651## 132                                    493  CH.sub.3  CH.sub.3                                                                                   ##STR652## 121 (sodium salt)                      494  CH.sub.3  n-C.sub.3 H.sub.7                                                                          ##STR653## 188 (sodium salt)                      495  CH.sub.3  CH.sub.3                                                                                   ##STR654## 175 (sodium salt)                      496                                                                                 ##STR655##                                                                             n-C.sub.3 H.sub.7                                                                          ##STR656## 111                                    497  CH.sub.3                                                                                 ##STR657##                                                                                ##STR658## 108                                    498  CH.sub.3  i-C.sub.4 H.sub.9                                                                          ##STR659## 129                                    499  CH.sub.3                                                                                 ##STR660##                                                                                ##STR661## 117                                    500  CH.sub.3  i-C.sub.4 H.sub.9                                                                          ##STR662##  96                                    501  CH.sub.3  CH.sub.2 CF.sub.3                                                                          ##STR663##                                        __________________________________________________________________________

STARTING SUBSTANCES OF THE FORMULA (II) Example (II-1) ##STR664##

A mixture of 5.0 g (0.02 mol) of1-phenoxycarbonyl-4-allyl-O-methyl-isosemicarbazide and 30 ml of tolueneis refluxed for 15 minutes and subsequently concentrated under a waterpump vacuum. The residue is triturated with diethyl ether/petroleumether, and the product which has been obtained in crystalline form isisolated by filtration with suction.

2.0 g (64% of theory) of4-allyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point111° C. are obtained.

Example (II-2) ##STR665##

50.2 g (0.33 mol) of phenyl hydrazinoformate and 36.6 g (0.33 mol, 93%strength) of trimethyl iminocarabonate are heated to 60° C. in 100 ml ofabsolute o-dichlorobenzene, and the mixture is stirred for 2 hours,during which process a clear mixture is stirred for 2 hours, duringwhich process a clear solution is formed. In the course of two hours, itis heated to 120° C., during which process methanol distilled off. Avacuum is applied carefully, during which process more methanol andfinally phenol distil off. Further distillation results in a fractionwhich solidifies in the receiving vessel in crystalline form.

After recrystallisation from toluene, 7.0 g (0.054 mol, 16% of theory)of 4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one of meltingpoint 142°-144° C. are obtained in the form of colourless crystals. Thiscompound in known from F. Arndt et al, Rev. faculte. Sci. Univ.Istanbul, 13A, 127 (1948).

Other examples of compounds of the formula (II) which can be preparedanalogously to Examples (II-1) and (II-2) are those listed in Table 6below. ##STR666##

                                      TABLE 6                                     __________________________________________________________________________    Examples of the starting substances of the                                    formula (II)                                                                  Example                    Melting                                            No.   R.sup.2  R.sup.3     point (°C.)                                 __________________________________________________________________________    II-3  CH.sub.3                                                                                           163                                                II-4  CH.sub.3 C.sub.3 H.sub.7                                                                           72                                                 II-5                                                                                 ##STR667##                                                                            CH.sub.3    149                                                II-6                                                                                 ##STR668##                                                                            C.sub.2 H.sub.5                                                                           130                                                II-7  CH(CH.sub.3).sub.2                                                                     CH.sub.3    80-81                                              II-8  C.sub.2 H.sub.5                                                                        CH.sub.3    (b.p.: 120° C.                                                         at 1.5 mbar)                                       II-9  C.sub.3 H.sub.7                                                                        CH.sub.3    (b.p.: 130-150° C.                                                     at 1.5 mbar)                                       II-10 CH.sub.3 C.sub.4 H.sub.9                                                                           152-153                                            II-11 (CH.sub.2).sub.3 OCH.sub.3                                                             CH.sub.3    84-85                                              II-12 CH.sub.3 C.sub.2 H.sub.5                                                                           (b.p.: 140-150° C.                                                     at 1.5 mbar)                                       II-13 CH(CH.sub.3).sub.2                                                                     C.sub.2 H.sub.5                                                                           66-67                                              II-14 C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                           (b.p.: 140-150° C.                                                     at 1.5 mbar)                                       II-15 CH.sub.2CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                           (b.p.: 150° C.                                                         at 1.5 mbar)                                       II-16                                                                                ##STR669##                                                                            n-C.sub.3 H.sub.7                                                                         100                                                II-17 CH.sub.3                                                                                ##STR670## 106                                                II-18 CH.sub.3 i-C.sub.3 H.sub.7                                                                         134                                                II-19 CH.sub.3 C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                          90                                                 II-20 CH.sub.3 C.sub.2 H.sub.4 OCH.sub.3                                                                 125                                                II-21 C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 OCH.sub.3                                                                 94                                                 II-22 C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                       92                                                 II-23 CH.sub.3                                                                                ##STR671## 73                                                 II-24 CH.sub.3                                                                                ##STR672## (Oil)                                              II-25 CH.sub.3                                                                                ##STR673## (Oil)                                              II-26 CH.sub.3                                                                                ##STR674## 37                                                 II-27 CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2                                                               (amorphous)                                        II-28 CH.sub.3 CH.sub.2 CHCH.sub.2                                                                       69                                                 II-29 CH.sub.3 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                      82                                                 II-30 CH.sub.3                                                                                ##STR675## 116                                                II-31 CH.sub.3 CH.sub.2 C(CH.sub.3).sub.3                                                                130                                                __________________________________________________________________________

INTERMEDIATES OF THE FORMULA (XVII) Example (XVII-1) ##STR676##

A mixture of 30.4 g (0.2 mol) of phenyl hydrazinoformate, 26.0 g (0.2mol) of methyl N-allyl-iminocarbonate and 150 ml of methanol is stirredfor 12 hours at 20° C. and subsequently concentrated under a water pumpvacuum. The residue is triturated with diethyl ether/ethanol (1/1 byvol.), and the crystalline product is isolated by filtration withsuction.

11.0 g (22% of theory) of1-phenoxycarbonyl-4-allyl-O-methyl-isosemicarbazide of melting point114° C. are obtained.

Other examples of compounds of the formula (IX) which can be preparedanalogously to Example (IX-1) are those listed in Table 5 below.##STR677##

                  TABLE 7                                                         ______________________________________                                        Examples of the compounds of the formula (XVII)                               Example                            Melting                                    No.       R.sup.2                                                                              R.sup.3  R.sup.4  point (°C.)                         ______________________________________                                        XVII-2    CH.sub.3                                                                             CH.sub.3                                                                                        123                                        XVII-3    C.sub.2 H.sub.5                                                                      CH.sub.3 C.sub.2 H.sub.5                                                                        137                                        XVII-4    CH.sub.3                                                                             CH.sub.3 CH.sub.3 134                                        XVII-5    CH.sub.3                                                                             CH.sub.3 C.sub.2 H.sub.5                                                                        135                                        XVII-6    C.sub.2 H.sub.5                                                                      CH.sub.3                                                                                ##STR678##                                                                            133-134                                    ______________________________________                                    

USE EXAMPLES

In the Use Examples, the following compound (A) is used as comparisonsubstance: ##STR679##

4-amino-5-methyl-2-phenylaminocarbonyl-2,4-dihydro-3-H-1,2,4-triazol-3-one(disclosed in EP-A 294,666).

Example A

    ______________________________________                                        Post-emergence test                                                           ______________________________________                                        Solvent:    5 parts by weight of acetone                                      Emulsifier: 1 part by weight of alkylaryl polyglycol                                      ether                                                             ______________________________________                                    

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is so chosen that the particularamounts of active compound desired are applied in 1000 l of water/ha.After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control. Thefigures denote: ##EQU1##

In this test, a clearly superior activity compared with the prior art isshown, for example, by the compounds of Preparation Examples 1 and 2.

Example B

    ______________________________________                                        Pre-emergence test                                                            ______________________________________                                        Solvent:    5 parts by weight of acetone                                      Emulsifier: 1 part by weight of alkylaryl polyglycol                                      ether                                                             ______________________________________                                    

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered with the preparation of the active compound. It is expedient tokeep constant the amount of water per unit area. The concentration ofthe active compound in the preparation is of no importance, only theamount of active compound applied per unit area being decisive. Afterthree weeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control. The figuresdenote: ##EQU2##

In this test, a powerful action against weeds combined with goodtolerance by crop plants such as, for example, barley, is shown, forexample, by the compound of Preparation Example 2.

USE EXAMPLES

In the second Use Examples, the following compound (C) is used ascomparison substance: ##STR680##

2-(2-chloro-phenylsulphonylaminocarbonyl)-4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one(disclosed in EP-A 341,489).

Example C

    ______________________________________                                        Post-emergence test                                                           ______________________________________                                        Solvent:    5 parts by weight of acetone                                      Emulsifier: 1 part by weight of alkylaryl polyglycol                                      ether                                                             ______________________________________                                    

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is so chosen that the particularamounts of active compound desired are applied in 1,000 l of water/ha.After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control. Thefigures denote: ##EQU3##

In this test, a considerably more powerful action against weeds than theknown compound (C) is shown, for example, by the compounds ofPreparation Examples 1, 2, 3, 53, 54, 55, 56, 57, 58, 64, 65 and 67,while having, in some cases, good crop plant compatibility.

Example D

    ______________________________________                                        Pre-emergence test                                                            ______________________________________                                        Solvent:    5 parts by weight of acetone                                      Emulsifier: 1 part by weight of alkylaryl polyglycol                                      ether                                                             ______________________________________                                    

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered with the preparation of the active compound. It is expedient tokeep constant the amount of water per unit area. The concentration ofthe active compound in the preparation is of no importance, only theamount of active compound applied per unit area being decisive. Afterthree weeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control. The figuresdenote: ##EQU4##

In this test, a considerably more powerful action against weeds than theknown compound (C) is shown, for example, by the compounds ofPreparation Examples 2, 54 and 69, while having, in some cases, goodcrop plant compatibility.

It will be understood that the specification and examples areillustrative but not limitative of the present invention and that otherembodiments within the spirit and scope of the invention will suggestthemselves to those skilled in the art.

What is claimed is:
 1. A triazolinone of the formula ##STR681## in whichR² represents amino, or represents C₁ -C₆ -alkyl which is optionallysubstituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy, C₁-C₄ -alkylcarbonyl or C₁ -C₄ -alkoxycarbonyl, or represents C₃ -C₆-alkenyl or C₃ -C₆ -alkinyl, each of which is optionally substituted byfluorine, chlorine and/or bromine, or represents C₃ -C₆ -cycloalkylwhich is optionally substituted by fluorine, chlorine, bromine and/or C₁-C₄ -alkyl, or C₁ -C₇ cycloalkyl-C₁ -C₆ -alkyl or represents phenyl-C₁-C₃ - alkylwhich is optionally substituted by fluorine, chlorine,bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxyand/or C₁ -C₄ -alkoxy-carbonyl, or represents phenyl which issubstituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl,trifluoromethyl, C₁ -C₄ -alkoxy, fluorine- and/or chlorine-substitutedC₁ -C₃ -alkoxy, C₁ -C₄ -alkylthio, fluorine- and/or chlorine-substitutedC₁ -C₃ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl and/orC₁ -C₄ -alkoxy-carbonyl, or represents C₁ -C₄ -alkylamino which isoptionally substituted by fluorine, cyano, C₁ -C₄ -alkoxy or C₁ -C₄-alkoxy-carbonyl, or represents C₃ -C₆ -cycloalkylamino or di-(C₁ -C₄-alkyl) -amino, and R³ represents C₁ -C₆ -alkyl which is optionallysubstituted by fluorine, chlorine, bromine, cyano, C₃ -C₆ -cycloalkyl,C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxycarbonyl, or represents C₃ -C₆ -alkenylor C₃ -C₆ -alkinyl, each of which is optionally substituted by fluorine,chlorine and/or bromine, or represents C₃ -C₆ -cycloalkyl which isoptionally substituted by fluorine, chlorine, bromine and/or C₁ -C₄-alkyl, or represents cyclohexenyl, or represents phenyl-C₁ -C₃ -alkylwhich is optionally substituted by fluorine, chlorine, bromine, cyano,nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy and/or C₁ -C₄-alkoxy-carbonyl, or represents phenyl which is optionally substitutedby fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl,trifluoromethyl, C₁ -C₄ -alkoxy, fluorine- and/or chlorine-substitutedC₁ -C₃ -alkoxy, C₁ -C₄ -alkylthio, fluorine- and/or chlorine-substitutedC₁ -C₃ -alkylthio, C₁ -C₄ -alkyl-sulphinyl, C₁ -C₄ -alkylsulphonyland/or C₁ -C₄ -alkoxy-carbonyl, provided that when R² is methyl, R³cannot be methyl.
 2. A triazolinone according to claim 1, whereinR²represents C₁ -C₃ alkyl, C₂ -C₃ alkenyl or C₃ -C₆ -cycloalkyl and R³represents C₁ -C₆ alkyl, C₂ -C₆ alkenyl or C₂ -C₆ alkynyl.
 3. Atriazolinone according to claim 1, whereinR² represents methyl orcyclopropyl and R³ represents methyl, ethyl, n-propyl, i-propyl, n-butylor allyl.
 4. A triazolinone according to claim 1, whereinR² representsethyl or allyl and R³ represents methyl, ethyl, n-propyl, i-propyl,n-butyl and allyl.
 5. A triazolinone according to claim 1, wherein##STR682##